Studies related to cephalosporins. Part 1. Solvolytic reactions of 3-bromomethylcephems with alcohols and phenols

Abstract

3-Bromomethyl-3-cephems are solvolyzed by alcohols, similarly to the Δ²-isomers. The yields are fairly good and this reaction represents a straightforward route to obtain 3-alkoxymethyl-3-cephems.

Both 3-bromomethyl-2-cephems and 3-bromomethyl-3-isomers react with a variety of phenols under solvolytic conditions, giving only C-substitution products. This reaction represents the sole example of C-alkylation of phenols by an allylic bromide under such mild conditions.