Switching pathways: room-temperature neutral solvolysis and substitution of amides |
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| Authors: | Hutchby Marc Houlden Chris E Haddow Mairi F Tyler Simon N G Lloyd-Jones Guy C Booker-Milburn Kevin I |
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| Affiliation: | School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, United Kingdom. |
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| Abstract: | Stick or twist: By introducing steric hindrance at the nitrogen atom, stable linear amides bearing an electron-withdrawing α-substituent (Z = Ar, PhSO(2), P(O)(OR)(2), CN, or CO(2)R) can be induced to undergo solvolysis and substitution reactions through an elimination-addition mechanism (see picture). Key to this process is a low barrier to rotation around the amide bond and the α-substituent?Z. |
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| Keywords: | amides solvolysis steric hindrance substituent effects substitution |
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