An investigation of the thermal decomposition of the methohydroxides and methodeuterio-oxides of some 5-N,N-dimethylaminopent-1-enes

Abstract

The base-catalysed thermal decomposition of a number of quaternary bases of the type (R¹)₂CCHC(R²)₂C(R³)₂CH₂NMe₃X^–(R¹= H, Me; R²= H, ²H; R³= H, ²H, Me; X = OH,O²H) has been investigated. It is shown that the reaction is initiated by attack of base (ŌH, Ō²H, ylide) on an allylic proton or [²H]. A mechanism for the reaction is suggested.