Substituent effects in the thermal rearrangement of bicyclo[2,1,1]hexenes
Abstract
anti-5-Methoxy-(2a) and 5-azidobicyclo[2,1,1]hexene (2b) rearrange cleanly at 30–50° to give exo-6-methoxy-(1c) and 6-azidobicyclo[3,1,0]hexene (1d) respectively; reduction of (2b) below 0° proceeds with rearrangement to 5-aminobicyclo[3,1,0]hexene.