From f58ad271909e39f9d839fde58dab7ac4f7ab6143 Mon Sep 17 00:00:00 2001
From: Fabian <132886103+FabianKruger@users.noreply.github.com>
Date: Tue, 4 Aug 2026 11:57:30 +0200
Subject: [PATCH] fixed stereochemistry of mitsunobu and added tests

---
 CHANGELOG.md                      |   4 +
 src/smartreact/data/templates.txt | 120 +++++++++++++++---------------
 tests/conftest.py                 |   4 +
 tests/test_enumerator.py          |  22 ++++++
 4 files changed, 90 insertions(+), 60 deletions(-)

diff --git a/CHANGELOG.md b/CHANGELOG.md
index 199b116..a7137a7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,10 @@ This follows the guideline on [keep a changelog](https://keepachangelog.com/en/1
 
 ## [Unreleased]
 
+### Fixed
+
+- Mitsunobu products now have the correct configuration at the carbinol carbon. The reaction proceeds by backside attack, so that centre inverts, but the templates left it unmarked and RDKit's default is to carry the reactant's configuration through unchanged — every stereodefined Mitsunobu product was the wrong enantiomer. All 60 mitsunobu templates now mark the centre as inverted relative to the input, so both input enantiomers are handled by the same template and an undefined centre stays undefined. No products are gained or lost; only their stereochemistry changes
+
 ### Changed
 
 - Reaction templates updated with the inert `;!$([a3])` qualifier removed (11,848 occurrences across 2,368 templates). `[a3]` means "aromatic *and* isotope 3", which no realistic molecule satisfies
diff --git a/src/smartreact/data/templates.txt b/src/smartreact/data/templates.txt
index bb5805d..84e4044 100644
--- a/src/smartreact/data/templates.txt
+++ b/src/smartreact/data/templates.txt
@@ -7040,66 +7040,66 @@ cross_electrophile_coupling	7038	CCc1c(Br)ccc2ccncc12.Brc1ccc2ccncc2c1CCc1c(Br)n
 cross_electrophile_coupling	7039	CCc1c(Br)ccc2ccncc12.Brc1ccc2ccncc2c1CCc1c(Br)ncc2ccccc12>>CCc1c2cnccc2ccc1c1ncc2ccccc2c1CCc1c(Br)ccc2ccncc12	[Br;$([Br][*;$([#6]);!$(*=*)]);$([$(*[$(c1cc2c(aaaa2)cc1)]),$(*[$(c(ccc2)c1c2aaaa1)]);!$([$(*[$(c1cc2c(cccc2)cc1)]),$(*[$(c(ccc2)c1c2cccc1)])])]):1][*:2].[Br;$([Br][*;$([#6]);!$(*=*)]);$([$(*[$(a1ac2c(cccc2)aa1)]),$(*[$(a(aaa2)c1c2cccc1)]);!$([$(*[$(c1cc2c(cccc2)cc1)]),$(*[$(c(ccc2)c1c2cccc1)]),$(*[$(c1cc2c(aaaa2)cc1)]),$(*[$(c(ccc2)c1c2aaaa1)])])]):3][a:4]>>[a:2][a:4]	X-Bromide_PheHet6.X-Bromide_Het6Phe
 cross_electrophile_coupling	7040	CCc1c(Br)ccc2ccncc12.Brc1cc2cocc2cc1CCc1c(Br)ccc2ccncc12>>CCc1c2cnccc2ccc1c1cc2cocc2cc1CCc1c(Br)ccc2ccncc12	[Br;$([Br][*;$([#6]);!$(*=*)]);$([$(*[$(c1cc2c(aaaa2)cc1)]),$(*[$(c(ccc2)c1c2aaaa1)]);!$([$(*[$(c1cc2c(cccc2)cc1)]),$(*[$(c(ccc2)c1c2cccc1)])])]):1][*:2].[Br;$([Br][*;$([#6]);!$(*=*)]);$([$(*[c;$(c1c2c(aaa2)ccc1)]),$(*[c;$(c1ccc2c(aaa2)c1)])]):3][a:4]>>[a:2][a:4]	X-Bromide_PheHet6.X-Bromide_PheHet5
 cross_electrophile_coupling	7041	CCc1c(Br)ccc2ccncc12.Brc1ccc2ccncc2c1CCCc1c(Br)ccc2ccncc12>>CCc1c2cnccc2ccc1c1ccc2ccncc2c1CCCc1c(Br)ccc2ccncc12	[Br;$([Br][*;$([#6]);!$(*=*)]);$([$(*[$(c1cc2c(aaaa2)cc1)]),$(*[$(c(ccc2)c1c2aaaa1)]);!$([$(*[$(c1cc2c(cccc2)cc1)]),$(*[$(c(ccc2)c1c2cccc1)])])]):1][*:2].[Br;$([Br][*;$([#6]);!$(*=*)]);$([$(*[$(c1cc2c(aaaa2)cc1)]),$(*[$(c(ccc2)c1c2aaaa1)]);!$([$(*[$(c1cc2c(cccc2)cc1)]),$(*[$(c(ccc2)c1c2cccc1)])])]):3][*:4]>>[a:2][a:4]	X-Bromide_PheHet6.X-Bromide_PheHet6
-mitsunobu	7042	CCc1ccccc1O.OCCCCCCc1ccccc1O>>CCc1ccccc1OCCCCCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6:4]>>[#6:2]O[#6:4]	Phenol.PrimaryAlcoholAliphatic
-mitsunobu	7043	CCc1ccccc1O.OCc1ccccc1CCCc1ccccc1O>>CCc1ccccc1OCc1ccccc1CCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6:4]>>[#6:2]O[#6:4]	Phenol.PrimaryAlcoholAromatic
-mitsunobu	7044	CCc1ccccc1O.CCC(O)CCCCCc1ccccc1O>>CCc1ccccc1OC(CC)CCCCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6:4]>>[#6:2]O[#6:4]	Phenol.SecondaryAlcoholAliphaticAcyclic
-mitsunobu	7045	CCc1ccccc1O.Oc1ccccc1CCC1CCC2C(C1)C(O)C1CCCCC12>>CCc1ccccc1OC1C2CCCCC2C2CCC(CCc3ccccc3O)CC21	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6:4]>>[#6:2]O[#6:4]	Phenol.SecondaryAlcoholAliphaticCyclic
-mitsunobu	7046	CCc1ccccc1O.Oc1ccccc1CCCc1ccccc1C(O)c1ccccc1>>CCc1ccccc1OC(c1ccccc1)c1ccccc1CCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6:4]>>[#6:2]O[#6:4]	Phenol.SecondaryAlcoholAromaticAcyclic
-mitsunobu	7047	CCc1ccccc1O.Oc1ccccc1CCc1ccc2c(c1)C(O)c1ccccc1-2>>CCc1ccccc1OC1c2ccccc2c2ccc(CCc3ccccc3O)cc21	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6:4]>>[#6:2]O[#6:4]	Phenol.SecondaryAlcoholAromaticCyclic
-mitsunobu	7048	CCc1ccccc1O.CCCC(O)c1ccccc1CCCc1ccccc1O>>CCCC(Oc1ccccc1CC)c1ccccc1CCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6:4]>>[#6:2]O[#6:4]	Phenol.SecondaryAlcoholMixAcyclic
-mitsunobu	7049	CCc1ccccc1O.Oc1ccccc1CCc1ccc2c(c1)C(O)C1CCCCC21>>CCc1ccccc1OC1c2cc(CCc3ccccc3O)ccc2C2CCCCC21	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6:4]>>[#6:2]O[#6:4]	Phenol.SecondaryAlcoholMixCyclic
-mitsunobu	7050	CCc1ccccc1O.CC(CCc1ccccc1O)CC(C)(C)O>>CCc1ccccc1OC(C)(C)CC(C)CCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]O[#6:4]	Phenol.TertiaryAlcoholAcyclic
-mitsunobu	7051	CCc1ccccc1O.CC1(O)CCCC(CCc2ccccc2O)C1>>CCc1ccccc1OC1(C)CCCC(CCc2ccccc2O)C1	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]O[#6:4]	Phenol.TertiaryAlcoholCyclic
-mitsunobu	7052	CCc1ccoc1O.OCCCCCCc1ccoc1O>>CCc1ccoc1OCCCCCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.PrimaryAlcoholAliphatic
-mitsunobu	7053	CCc1ccoc1O.OCc1ccccc1CCCc1ccoc1O>>CCc1ccoc1OCc1ccccc1CCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.PrimaryAlcoholAromatic
-mitsunobu	7054	CCc1ccoc1O.CCC(O)CCCCCc1ccoc1O>>CCc1ccoc1OC(CC)CCCCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholAliphaticAcyclic
-mitsunobu	7055	CCc1ccoc1O.Oc1occc1CCC1CCC2C(C1)C(O)C1CCCCC12>>CCc1ccoc1OC1C2CCCCC2C2CCC(CCc3ccoc3O)CC21	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholAliphaticCyclic
-mitsunobu	7056	CCc1ccoc1O.Oc1occc1CCCc1ccccc1C(O)c1ccccc1>>CCc1ccoc1OC(c1ccccc1)c1ccccc1CCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholAromaticAcyclic
-mitsunobu	7057	CCc1ccoc1O.Oc1occc1CCc1ccc2c(c1)C(O)c1ccccc1-2>>CCc1ccoc1OC1c2ccccc2c2ccc(CCc3ccoc3O)cc21	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholAromaticCyclic
-mitsunobu	7058	CCc1ccoc1O.CCCC(O)c1ccccc1CCCc1ccoc1O>>CCCC(Oc1occc1CC)c1ccccc1CCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholMixAcyclic
-mitsunobu	7059	CCc1ccoc1O.Oc1occc1CCc1ccc2c(c1)C(O)C1CCCCC21>>CCc1ccoc1OC1c2cc(CCc3ccoc3O)ccc2C2CCCCC21	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholMixCyclic
-mitsunobu	7060	CCc1ccoc1O.CC(CCc1ccoc1O)CC(C)(C)O>>CCc1ccoc1OC(C)(C)CC(C)CCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.TertiaryAlcoholAcyclic
-mitsunobu	7061	CCc1ccoc1O.CC1(O)CCCC(CCc2ccoc2O)C1>>CCc1ccoc1OC1(C)CCCC(CCc2ccoc2O)C1	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic5membered.TertiaryAlcoholCyclic
-mitsunobu	7062	CCc1cccnc1O.OCCCCCCc1cccnc1O>>CCc1cccnc1OCCCCCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.PrimaryAlcoholAliphatic
-mitsunobu	7063	CCc1cccnc1O.OCc1ccccc1CCCc1cccnc1O>>CCc1cccnc1OCc1ccccc1CCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.PrimaryAlcoholAromatic
-mitsunobu	7064	CCc1cccnc1O.CCC(O)CCCCCc1cccnc1O>>CCc1cccnc1OC(CC)CCCCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholAliphaticAcyclic
-mitsunobu	7065	CCc1cccnc1O.Oc1ncccc1CCC1CCC2C(C1)C(O)C1CCCCC12>>CCc1cccnc1OC1C2CCCCC2C2CCC(CCc3cccnc3O)CC21	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholAliphaticCyclic
-mitsunobu	7066	CCc1cccnc1O.Oc1ncccc1CCCc1ccccc1C(O)c1ccccc1>>CCc1cccnc1OC(c1ccccc1)c1ccccc1CCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholAromaticAcyclic
-mitsunobu	7067	CCc1cccnc1O.Oc1ncccc1CCc1ccc2c(c1)C(O)c1ccccc1-2>>CCc1cccnc1OC1c2ccccc2c2ccc(CCc3cccnc3O)cc21	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholAromaticCyclic
-mitsunobu	7068	CCc1cccnc1O.CCCC(O)c1ccccc1CCCc1cccnc1O>>CCCC(Oc1ncccc1CC)c1ccccc1CCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholMixAcyclic
-mitsunobu	7069	CCc1cccnc1O.Oc1ncccc1CCc1ccc2c(c1)C(O)C1CCCCC21>>CCc1cccnc1OC1c2cc(CCc3cccnc3O)ccc2C2CCCCC21	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholMixCyclic
-mitsunobu	7070	CCc1cccnc1O.CC(CCc1cccnc1O)CC(C)(C)O>>CCc1cccnc1OC(C)(C)CC(C)CCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.TertiaryAlcoholAcyclic
-mitsunobu	7071	CCc1cccnc1O.CC1(O)CCCC(CCc2cccnc2O)C1>>CCc1cccnc1OC1(C)CCCC(CCc2cccnc2O)C1	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]O[#6:4]	PhenolHeteroaromatic6membered.TertiaryAlcoholCyclic
-mitsunobu	7072	CCc1ccccc1S.OCCCCCCc1ccccc1S>>CCc1ccccc1SCCCCCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.PrimaryAlcoholAliphatic
-mitsunobu	7073	CCc1ccccc1S.OCc1ccccc1CCCc1ccccc1S>>CCc1ccccc1SCc1ccccc1CCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.PrimaryAlcoholAromatic
-mitsunobu	7074	CCc1ccccc1S.CCC(O)CCCCCc1ccccc1S>>CCc1ccccc1SC(CC)CCCCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.SecondaryAlcoholAliphaticAcyclic
-mitsunobu	7075	CCc1ccccc1S.OC1C2CCCCC2C2CCC(CCc3ccccc3S)CC12>>CCc1ccccc1SC1C2CCCCC2C2CCC(CCc3ccccc3S)CC21	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.SecondaryAlcoholAliphaticCyclic
-mitsunobu	7076	CCc1ccccc1S.OC(c1ccccc1)c1ccccc1CCCc1ccccc1S>>CCc1ccccc1SC(c1ccccc1)c1ccccc1CCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.SecondaryAlcoholAromaticAcyclic
-mitsunobu	7077	CCc1ccccc1S.OC1c2ccccc2-c2ccc(CCc3ccccc3S)cc21>>CCc1ccccc1SC1c2ccccc2c2ccc(CCc3ccccc3S)cc21	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.SecondaryAlcoholAromaticCyclic
-mitsunobu	7078	CCc1ccccc1S.CCCC(O)c1ccccc1CCCc1ccccc1S>>CCCC(Sc1ccccc1CC)c1ccccc1CCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.SecondaryAlcoholMixAcyclic
-mitsunobu	7079	CCc1ccccc1S.OC1c2cc(CCc3ccccc3S)ccc2C2CCCCC12>>CCc1ccccc1SC1c2cc(CCc3ccccc3S)ccc2C2CCCCC21	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.SecondaryAlcoholMixCyclic
-mitsunobu	7080	CCc1ccccc1S.CC(CCc1ccccc1S)CC(C)(C)O>>CCc1ccccc1SC(C)(C)CC(C)CCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.TertiaryAlcoholAcyclic
-mitsunobu	7081	CCc1ccccc1S.CC1(O)CCCC(CCc2ccccc2S)C1>>CCc1ccccc1SC1(C)CCCC(CCc2ccccc2S)C1	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]S[#6:4]	Thiophenol.TertiaryAlcoholCyclic
-mitsunobu	7082	CCc1ccoc1S.OCCCCCCc1ccoc1S>>CCc1ccoc1SCCCCCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.PrimaryAlcoholAliphatic
-mitsunobu	7083	CCc1ccoc1S.OCc1ccccc1CCCc1ccoc1S>>CCc1ccoc1SCc1ccccc1CCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.PrimaryAlcoholAromatic
-mitsunobu	7084	CCc1ccoc1S.CCC(O)CCCCCc1ccoc1S>>CCc1ccoc1SC(CC)CCCCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholAliphaticAcyclic
-mitsunobu	7085	CCc1ccoc1S.OC1C2CCCCC2C2CCC(CCc3ccoc3S)CC12>>CCc1ccoc1SC1C2CCCCC2C2CCC(CCc3ccoc3S)CC21	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholAliphaticCyclic
-mitsunobu	7086	CCc1ccoc1S.OC(c1ccccc1)c1ccccc1CCCc1ccoc1S>>CCc1ccoc1SC(c1ccccc1)c1ccccc1CCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholAromaticAcyclic
-mitsunobu	7087	CCc1ccoc1S.OC1c2ccccc2-c2ccc(CCc3ccoc3S)cc21>>CCc1ccoc1SC1c2ccccc2c2ccc(CCc3ccoc3S)cc21	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholAromaticCyclic
-mitsunobu	7088	CCc1ccoc1S.CCCC(O)c1ccccc1CCCc1ccoc1S>>CCCC(Sc1occc1CC)c1ccccc1CCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholMixAcyclic
-mitsunobu	7089	CCc1ccoc1S.OC1c2cc(CCc3ccoc3S)ccc2C2CCCCC12>>CCc1ccoc1SC1c2cc(CCc3ccoc3S)ccc2C2CCCCC21	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholMixCyclic
-mitsunobu	7090	CCc1ccoc1S.CC(CCc1ccoc1S)CC(C)(C)O>>CCc1ccoc1SC(C)(C)CC(C)CCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.TertiaryAlcoholAcyclic
-mitsunobu	7091	CCc1ccoc1S.CC1(O)CCCC(CCc2ccoc2S)C1>>CCc1ccoc1SC1(C)CCCC(CCc2ccoc2S)C1	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic5membered.TertiaryAlcoholCyclic
-mitsunobu	7092	CCc1cccnc1S.OCCCCCCc1cccnc1S>>CCc1cccnc1SCCCCCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.PrimaryAlcoholAliphatic
-mitsunobu	7093	CCc1cccnc1S.OCc1ccccc1CCCc1cccnc1S>>CCc1cccnc1SCc1ccccc1CCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.PrimaryAlcoholAromatic
-mitsunobu	7094	CCc1cccnc1S.CCC(O)CCCCCc1cccnc1S>>CCc1cccnc1SC(CC)CCCCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholAliphaticAcyclic
-mitsunobu	7095	CCc1cccnc1S.OC1C2CCCCC2C2CCC(CCc3cccnc3S)CC12>>CCc1cccnc1SC1C2CCCCC2C2CCC(CCc3cccnc3S)CC21	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholAliphaticCyclic
-mitsunobu	7096	CCc1cccnc1S.OC(c1ccccc1)c1ccccc1CCCc1cccnc1S>>CCc1cccnc1SC(c1ccccc1)c1ccccc1CCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholAromaticAcyclic
-mitsunobu	7097	CCc1cccnc1S.OC1c2ccccc2-c2ccc(CCc3cccnc3S)cc21>>CCc1cccnc1SC1c2ccccc2c2ccc(CCc3cccnc3S)cc21	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholAromaticCyclic
-mitsunobu	7098	CCc1cccnc1S.CCCC(O)c1ccccc1CCCc1cccnc1S>>CCCC(Sc1ncccc1CC)c1ccccc1CCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholMixAcyclic
-mitsunobu	7099	CCc1cccnc1S.OC1c2cc(CCc3cccnc3S)ccc2C2CCCCC12>>CCc1cccnc1SC1c2cc(CCc3cccnc3S)ccc2C2CCCCC21	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholMixCyclic
-mitsunobu	7100	CCc1cccnc1S.CC(CCc1cccnc1S)CC(C)(C)O>>CCc1cccnc1SC(C)(C)CC(C)CCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.TertiaryAlcoholAcyclic
-mitsunobu	7101	CCc1cccnc1S.CC1(O)CCCC(CCc2cccnc2S)C1>>CCc1cccnc1SC1(C)CCCC(CCc2cccnc2S)C1	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6:4]>>[#6:2]S[#6:4]	ThiophenolHeteroaromatic6membered.TertiaryAlcoholCyclic
+mitsunobu	7042	CCc1ccccc1O.OCCCCCCc1ccccc1O>>CCc1ccccc1OCCCCCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.PrimaryAlcoholAliphatic
+mitsunobu	7043	CCc1ccccc1O.OCc1ccccc1CCCc1ccccc1O>>CCc1ccccc1OCc1ccccc1CCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.PrimaryAlcoholAromatic
+mitsunobu	7044	CCc1ccccc1O.CCC(O)CCCCCc1ccccc1O>>CCc1ccccc1OC(CC)CCCCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.SecondaryAlcoholAliphaticAcyclic
+mitsunobu	7045	CCc1ccccc1O.Oc1ccccc1CCC1CCC2C(C1)C(O)C1CCCCC12>>CCc1ccccc1OC1C2CCCCC2C2CCC(CCc3ccccc3O)CC21	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.SecondaryAlcoholAliphaticCyclic
+mitsunobu	7046	CCc1ccccc1O.Oc1ccccc1CCCc1ccccc1C(O)c1ccccc1>>CCc1ccccc1OC(c1ccccc1)c1ccccc1CCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.SecondaryAlcoholAromaticAcyclic
+mitsunobu	7047	CCc1ccccc1O.Oc1ccccc1CCc1ccc2c(c1)C(O)c1ccccc1-2>>CCc1ccccc1OC1c2ccccc2c2ccc(CCc3ccccc3O)cc21	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.SecondaryAlcoholAromaticCyclic
+mitsunobu	7048	CCc1ccccc1O.CCCC(O)c1ccccc1CCCc1ccccc1O>>CCCC(Oc1ccccc1CC)c1ccccc1CCCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.SecondaryAlcoholMixAcyclic
+mitsunobu	7049	CCc1ccccc1O.Oc1ccccc1CCc1ccc2c(c1)C(O)C1CCCCC21>>CCc1ccccc1OC1c2cc(CCc3ccccc3O)ccc2C2CCCCC21	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.SecondaryAlcoholMixCyclic
+mitsunobu	7050	CCc1ccccc1O.CC(CCc1ccccc1O)CC(C)(C)O>>CCc1ccccc1OC(C)(C)CC(C)CCc1ccccc1O	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.TertiaryAlcoholAcyclic
+mitsunobu	7051	CCc1ccccc1O.CC1(O)CCCC(CCc2ccccc2O)C1>>CCc1ccccc1OC1(C)CCCC(CCc2ccccc2O)C1	[O;H1;D1;$(Oc1ccccc1),$(Oc1cccc1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]O[#6@@:4]	Phenol.TertiaryAlcoholCyclic
+mitsunobu	7052	CCc1ccoc1O.OCCCCCCc1ccoc1O>>CCc1ccoc1OCCCCCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.PrimaryAlcoholAliphatic
+mitsunobu	7053	CCc1ccoc1O.OCc1ccccc1CCCc1ccoc1O>>CCc1ccoc1OCc1ccccc1CCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.PrimaryAlcoholAromatic
+mitsunobu	7054	CCc1ccoc1O.CCC(O)CCCCCc1ccoc1O>>CCc1ccoc1OC(CC)CCCCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholAliphaticAcyclic
+mitsunobu	7055	CCc1ccoc1O.Oc1occc1CCC1CCC2C(C1)C(O)C1CCCCC12>>CCc1ccoc1OC1C2CCCCC2C2CCC(CCc3ccoc3O)CC21	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholAliphaticCyclic
+mitsunobu	7056	CCc1ccoc1O.Oc1occc1CCCc1ccccc1C(O)c1ccccc1>>CCc1ccoc1OC(c1ccccc1)c1ccccc1CCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholAromaticAcyclic
+mitsunobu	7057	CCc1ccoc1O.Oc1occc1CCc1ccc2c(c1)C(O)c1ccccc1-2>>CCc1ccoc1OC1c2ccccc2c2ccc(CCc3ccoc3O)cc21	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholAromaticCyclic
+mitsunobu	7058	CCc1ccoc1O.CCCC(O)c1ccccc1CCCc1ccoc1O>>CCCC(Oc1occc1CC)c1ccccc1CCCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholMixAcyclic
+mitsunobu	7059	CCc1ccoc1O.Oc1occc1CCc1ccc2c(c1)C(O)C1CCCCC21>>CCc1ccoc1OC1c2cc(CCc3ccoc3O)ccc2C2CCCCC21	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.SecondaryAlcoholMixCyclic
+mitsunobu	7060	CCc1ccoc1O.CC(CCc1ccoc1O)CC(C)(C)O>>CCc1ccoc1OC(C)(C)CC(C)CCc1ccoc1O	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.TertiaryAlcoholAcyclic
+mitsunobu	7061	CCc1ccoc1O.CC1(O)CCCC(CCc2ccoc2O)C1>>CCc1ccoc1OC1(C)CCCC(CCc2ccoc2O)C1	[O;H1;D1;!$(Oc1cccc1);$(Oc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic5membered.TertiaryAlcoholCyclic
+mitsunobu	7062	CCc1cccnc1O.OCCCCCCc1cccnc1O>>CCc1cccnc1OCCCCCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.PrimaryAlcoholAliphatic
+mitsunobu	7063	CCc1cccnc1O.OCc1ccccc1CCCc1cccnc1O>>CCc1cccnc1OCc1ccccc1CCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.PrimaryAlcoholAromatic
+mitsunobu	7064	CCc1cccnc1O.CCC(O)CCCCCc1cccnc1O>>CCc1cccnc1OC(CC)CCCCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholAliphaticAcyclic
+mitsunobu	7065	CCc1cccnc1O.Oc1ncccc1CCC1CCC2C(C1)C(O)C1CCCCC12>>CCc1cccnc1OC1C2CCCCC2C2CCC(CCc3cccnc3O)CC21	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholAliphaticCyclic
+mitsunobu	7066	CCc1cccnc1O.Oc1ncccc1CCCc1ccccc1C(O)c1ccccc1>>CCc1cccnc1OC(c1ccccc1)c1ccccc1CCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholAromaticAcyclic
+mitsunobu	7067	CCc1cccnc1O.Oc1ncccc1CCc1ccc2c(c1)C(O)c1ccccc1-2>>CCc1cccnc1OC1c2ccccc2c2ccc(CCc3cccnc3O)cc21	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholAromaticCyclic
+mitsunobu	7068	CCc1cccnc1O.CCCC(O)c1ccccc1CCCc1cccnc1O>>CCCC(Oc1ncccc1CC)c1ccccc1CCCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholMixAcyclic
+mitsunobu	7069	CCc1cccnc1O.Oc1ncccc1CCc1ccc2c(c1)C(O)C1CCCCC21>>CCc1cccnc1OC1c2cc(CCc3cccnc3O)ccc2C2CCCCC21	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.SecondaryAlcoholMixCyclic
+mitsunobu	7070	CCc1cccnc1O.CC(CCc1cccnc1O)CC(C)(C)O>>CCc1cccnc1OC(C)(C)CC(C)CCc1cccnc1O	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.TertiaryAlcoholAcyclic
+mitsunobu	7071	CCc1cccnc1O.CC1(O)CCCC(CCc2cccnc2O)C1>>CCc1cccnc1OC1(C)CCCC(CCc2cccnc2O)C1	[O;H1;D1;!$(Oc1ccccc1);$(Oc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]O[#6@@:4]	PhenolHeteroaromatic6membered.TertiaryAlcoholCyclic
+mitsunobu	7072	CCc1ccccc1S.OCCCCCCc1ccccc1S>>CCc1ccccc1SCCCCCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.PrimaryAlcoholAliphatic
+mitsunobu	7073	CCc1ccccc1S.OCc1ccccc1CCCc1ccccc1S>>CCc1ccccc1SCc1ccccc1CCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.PrimaryAlcoholAromatic
+mitsunobu	7074	CCc1ccccc1S.CCC(O)CCCCCc1ccccc1S>>CCc1ccccc1SC(CC)CCCCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.SecondaryAlcoholAliphaticAcyclic
+mitsunobu	7075	CCc1ccccc1S.OC1C2CCCCC2C2CCC(CCc3ccccc3S)CC12>>CCc1ccccc1SC1C2CCCCC2C2CCC(CCc3ccccc3S)CC21	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.SecondaryAlcoholAliphaticCyclic
+mitsunobu	7076	CCc1ccccc1S.OC(c1ccccc1)c1ccccc1CCCc1ccccc1S>>CCc1ccccc1SC(c1ccccc1)c1ccccc1CCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.SecondaryAlcoholAromaticAcyclic
+mitsunobu	7077	CCc1ccccc1S.OC1c2ccccc2-c2ccc(CCc3ccccc3S)cc21>>CCc1ccccc1SC1c2ccccc2c2ccc(CCc3ccccc3S)cc21	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.SecondaryAlcoholAromaticCyclic
+mitsunobu	7078	CCc1ccccc1S.CCCC(O)c1ccccc1CCCc1ccccc1S>>CCCC(Sc1ccccc1CC)c1ccccc1CCCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.SecondaryAlcoholMixAcyclic
+mitsunobu	7079	CCc1ccccc1S.OC1c2cc(CCc3ccccc3S)ccc2C2CCCCC12>>CCc1ccccc1SC1c2cc(CCc3ccccc3S)ccc2C2CCCCC21	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.SecondaryAlcoholMixCyclic
+mitsunobu	7080	CCc1ccccc1S.CC(CCc1ccccc1S)CC(C)(C)O>>CCc1ccccc1SC(C)(C)CC(C)CCc1ccccc1S	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.TertiaryAlcoholAcyclic
+mitsunobu	7081	CCc1ccccc1S.CC1(O)CCCC(CCc2ccccc2S)C1>>CCc1ccccc1SC1(C)CCCC(CCc2ccccc2S)C1	[S;H1;D1;$(Sc1ccccc1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]S[#6@@:4]	Thiophenol.TertiaryAlcoholCyclic
+mitsunobu	7082	CCc1ccoc1S.OCCCCCCc1ccoc1S>>CCc1ccoc1SCCCCCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.PrimaryAlcoholAliphatic
+mitsunobu	7083	CCc1ccoc1S.OCc1ccccc1CCCc1ccoc1S>>CCc1ccoc1SCc1ccccc1CCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.PrimaryAlcoholAromatic
+mitsunobu	7084	CCc1ccoc1S.CCC(O)CCCCCc1ccoc1S>>CCc1ccoc1SC(CC)CCCCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholAliphaticAcyclic
+mitsunobu	7085	CCc1ccoc1S.OC1C2CCCCC2C2CCC(CCc3ccoc3S)CC12>>CCc1ccoc1SC1C2CCCCC2C2CCC(CCc3ccoc3S)CC21	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholAliphaticCyclic
+mitsunobu	7086	CCc1ccoc1S.OC(c1ccccc1)c1ccccc1CCCc1ccoc1S>>CCc1ccoc1SC(c1ccccc1)c1ccccc1CCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholAromaticAcyclic
+mitsunobu	7087	CCc1ccoc1S.OC1c2ccccc2-c2ccc(CCc3ccoc3S)cc21>>CCc1ccoc1SC1c2ccccc2c2ccc(CCc3ccoc3S)cc21	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholAromaticCyclic
+mitsunobu	7088	CCc1ccoc1S.CCCC(O)c1ccccc1CCCc1ccoc1S>>CCCC(Sc1occc1CC)c1ccccc1CCCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholMixAcyclic
+mitsunobu	7089	CCc1ccoc1S.OC1c2cc(CCc3ccoc3S)ccc2C2CCCCC12>>CCc1ccoc1SC1c2cc(CCc3ccoc3S)ccc2C2CCCCC21	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.SecondaryAlcoholMixCyclic
+mitsunobu	7090	CCc1ccoc1S.CC(CCc1ccoc1S)CC(C)(C)O>>CCc1ccoc1SC(C)(C)CC(C)CCc1ccoc1S	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.TertiaryAlcoholAcyclic
+mitsunobu	7091	CCc1ccoc1S.CC1(O)CCCC(CCc2ccoc2S)C1>>CCc1ccoc1SC1(C)CCCC(CCc2ccoc2S)C1	[S;H1;D1;!$(Sc1cccc1);$(Sc1aaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic5membered.TertiaryAlcoholCyclic
+mitsunobu	7092	CCc1cccnc1S.OCCCCCCc1cccnc1S>>CCc1cccnc1SCCCCCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;D2,D1;!$(C[a])]);!$(OC=*);!$(OC#*):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.PrimaryAlcoholAliphatic
+mitsunobu	7093	CCc1cccnc1S.OCc1ccccc1CCCc1cccnc1S>>CCc1cccnc1SCc1ccccc1CCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;D2][a]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.PrimaryAlcoholAromatic
+mitsunobu	7094	CCc1cccnc1S.CCC(O)CCCCCc1cccnc1S>>CCc1cccnc1SC(CC)CCCCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([A])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholAliphaticAcyclic
+mitsunobu	7095	CCc1cccnc1S.OC1C2CCCCC2C2CCC(CCc3cccnc3S)CC12>>CCc1cccnc1SC1C2CCCCC2C2CCC(CCc3cccnc3S)CC21	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([A])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholAliphaticCyclic
+mitsunobu	7096	CCc1cccnc1S.OC(c1ccccc1)c1ccccc1CCCc1cccnc1S>>CCc1cccnc1SC(c1ccccc1)c1ccccc1CCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[a]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholAromaticAcyclic
+mitsunobu	7097	CCc1cccnc1S.OC1c2ccccc2-c2ccc(CCc3cccnc3S)cc21>>CCc1cccnc1SC1c2ccccc2c2ccc(CCc3cccnc3S)cc21	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[a]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholAromaticCyclic
+mitsunobu	7098	CCc1cccnc1S.CCCC(O)c1ccccc1CCCc1cccnc1S>>CCCC(Sc1ncccc1CC)c1ccccc1CCCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D3]([a])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholMixAcyclic
+mitsunobu	7099	CCc1cccnc1S.OC1c2cc(CCc3cccnc3S)ccc2C2CCCCC12>>CCc1cccnc1SC1c2cc(CCc3cccnc3S)ccc2C2CCCCC21	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D3]([a])[A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.SecondaryAlcoholMixCyclic
+mitsunobu	7100	CCc1cccnc1S.CC(CCc1cccnc1S)CC(C)(C)O>>CCc1cccnc1SC(C)(C)CC(C)CCc1cccnc1S	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;!R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.TertiaryAlcoholAcyclic
+mitsunobu	7101	CCc1cccnc1S.CC1(O)CCCC(CCc2cccnc2S)C1>>CCc1cccnc1SC1(C)CCCC(CCc2cccnc2S)C1	[S;H1;D1;!$(Sc1ccccc1);$(Sc1aaaaa1):1][#6:2].[O;H1;D1;$(O[C;R;D4]([a,A])([a,A])[a,A]):3][#6@:4]>>[#6:2]S[#6@@:4]	ThiophenolHeteroaromatic6membered.TertiaryAlcoholCyclic
 oxadiazole_condensation	7102	CCCCC(=O)O.NNC(=O)CCCCCCC(=O)O>>CCCCc1nnc(CCCCCCC(=O)O)o1	[O;D1;$(O[C;D2,D3;$(C(=O));!$(C(O)(=O)[!#6])]);$([!$(**[C]=[C]);!$(**[C]#[C]);!$(**[C]#[N]);!$(**a)]):1]C(=O)[*:2].[N;D1;$(N[N;D2]C(=[O,S])):3]NC(=O)[*:4]>>[*:2]c1:n:n:c(o:1)[*:4]	Acid_SaturatedAliphatic.HydrazineTerminalCarbamoyl
 oxadiazole_condensation	7103	CCCCC(=O)O.NC(CCCCCCC(=O)O)=NO>>CCCCc1nnc(CCCCCCC(=O)O)o1	[O;D1;$(O[C;D2,D3;$(C(=O));!$(C(O)(=O)[!#6])]);$([!$(**[C]=[C]);!$(**[C]#[C]);!$(**[C]#[N]);!$(**a)]):1]C(=O)[*:2].[O;D1;$(ON=[C;D3][N;D1]):3]N=C(N)[#6:4]>>[*:2]c1:n:n:c(o:1)[*:4]	Acid_SaturatedAliphatic.HydroxyAmidine
 oxadiazole_condensation	7104	CCC=CC(=O)O.NNC(=O)CCCCC=CC(=O)O>>CCC=Cc1nnc(CCCCC=CC(=O)O)o1	[O;D1;$(O[C;D2,D3;$(C(=O));!$(C(O)(=O)[!#6])]);$([$(**[C]=[C]),$(**[C]#[C]),$(**[C]#[N]);!$(**a)]):1]C(=O)[*:2].[N;D1;$(N[N;D2]C(=[O,S])):3]NC(=O)[*:4]>>[*:2]c1:n:n:c(o:1)[*:4]	Acid_UnsaturatedAliphatic.HydrazineTerminalCarbamoyl
diff --git a/tests/conftest.py b/tests/conftest.py
index f701ad3..b68626d 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -11,6 +11,10 @@
 BIPHENYL = "c1ccc(-c2ccccc2)cc1"
 ETHANOL = "CCO"
 DIMETHYLAMINE = "CNC"
+PHENOL = "Oc1ccccc1"
+S_BUTAN_2_OL = "C[C@H](O)CC"
+R_BUTAN_2_OL = "C[C@@H](O)CC"
+BUTAN_2_OL = "CCC(O)C"
 
 
 @pytest.fixture(scope="session")
diff --git a/tests/test_enumerator.py b/tests/test_enumerator.py
index d1aa087..cee93a1 100644
--- a/tests/test_enumerator.py
+++ b/tests/test_enumerator.py
@@ -15,11 +15,15 @@
     ACETIC_ACID,
     BIPHENYL,
     BROMOBENZENE,
+    BUTAN_2_OL,
     DIMETHYLAMINE,
     ETHANOL,
     ETHYLAMINE,
     IODOBENZENE,
+    PHENOL,
     PHENYLBORONIC_ACID,
+    R_BUTAN_2_OL,
+    S_BUTAN_2_OL,
 )
 
 
@@ -52,6 +56,24 @@ def test_no_reaction(self, enumerator: ReactionEnumerator):
         assert results == []
 
 
+class TestMitsunobuStereochemistry:
+    """Mitsunobu displaces the alcohol by backside attack, so the carbinol carbon inverts."""
+
+    def test_s_alcohol_gives_r_ether(self, enumerator: ReactionEnumerator):
+        products = enumerator.products_for_pair(PHENOL, S_BUTAN_2_OL)
+        assert products == ["CC[C@@H](C)Oc1ccccc1"]
+
+    def test_r_alcohol_gives_s_ether(self, enumerator: ReactionEnumerator):
+        """The same templates must invert the opposite enantiomer too, not fix an absolute tag."""
+        products = enumerator.products_for_pair(PHENOL, R_BUTAN_2_OL)
+        assert products == ["CC[C@H](C)Oc1ccccc1"]
+
+    def test_undefined_centre_stays_undefined(self, enumerator: ReactionEnumerator):
+        """Inverting an unknown configuration is still unknown; no stereochemistry is invented."""
+        products = enumerator.products_for_pair(PHENOL, BUTAN_2_OL)
+        assert products == ["CCC(C)Oc1ccccc1"]
+
+
 class TestProductsForPair:
     def test_returns_strings(self, enumerator: ReactionEnumerator):
         products = enumerator.products_for_pair(BROMOBENZENE, PHENYLBORONIC_ACID)