Metal-Ammonia Reduction and Reductive Alkylation of N-Alkylnaphthalenesulfonamides. A New Route to Substituted Naphthalenes

Article abstract of DOI:10.1021/jo00035a018

Conditions have been found for 1,4-reduction of aromatic sulfomamides (conveniently monitored by electrical conductivity), using metals in THF/liquid ammonia on the pre-formed N-lithium salts (BuLi), without concomitant C-S reductive cleavage.The resultin