title: Switching pathways: room-temperature neutral solvolysis and substitution of amides.
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.
authors: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, United Kingdom.
authors: Marc
authors: M
authors: Hutchby
authors: Chris E
authors: CE
authors: Houlden
authors: Mairi F
authors: MF
authors: Haddow
authors: Simon N G
authors: SN
authors: Tyler
authors: Guy C
authors: GC
authors: Lloyd-Jones
authors: Kevin I
authors: KI
authors: Booker-Milburn
mesh_terms: D000577:Amides / Q000737:chemistry*; D004583:Electrons; D009584:Nitrogen / Q000737:chemistry*; D013696:Temperature
chemical_list: D000577:Amides; D009584:Nitrogen