Reduction of Alkyl-Substituted Butadienes by Sodium in Liquid Ammonia

Article abstract of DOI:10.1021/jo01300a008

Six alkyl-substituted butadienes have been reduced by sodium in liquid ammonia to determine the relative importance of 1,2 and 1,4 reduction pathways and, for the latter, whether the cisoid or transoid state of the butadiene preferentially is reduced.The 1,4 reduction predominates in all cases and especially so when a terminal methylene is present.For alkylbutadienes which have no steric constraints preventing the cisoid conformation, 1,4 reduction of the cisoid conformation is preferred.