1360789-08-7Relevant articles and documents
Switching pathways: Room-temperature neutral solvolysis and substitution of amides
Hutchby, Marc,Houlden, Chris E.,Haddow, Mairi F.,Tyler, Simon N. G.,Lloyd-Jones, Guy C.,Booker-Milburn, Kevin I.
supporting information; experimental part, p. 548 - 551 (2012/02/04)
Stick or twist: By introducing steric hindrance at the nitrogen atom, stable linear amides bearing an electron-withdrawing α-substituent (Z=Ar, PhSO2, P(O)(OR)2, CN, or CO2R) 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-substituentZ. Copyright