Welcome to Wednesday night problem session boys and girls! This new series will push your chemical abilities to the limit, and may amuse and amaze your friends! Without further ado, today’s problem comes from Harvard’s Challenging CCB Problems Database, which is pretty much the greatest website ever constructed.
Mapp et al. have described a synthesis of allylic amines from allylic alcohols using the reaction shown below.Note the sweet E/Z ratio they obtained. Provide a mechanism for this transformation and an explanation for the observed E selectivity.
Hint: the mechanism involves a rather curious intermediate. Don’t cheat now! Answers coming soon!