Thioanhydrides. 3. Synthesis, Properties, and Diels-Alder Reactions of Sulfur Analogues of 1,8-Naphthalic Anhydride

Article abstract of DOI:10.1021/jo00281a011

All five possible sulfur analogues of 1,8-naphthalic anhydride have been synthesized by practical procedures, starting from 1,8-naphthalic anhydride.The thionoanhydrides containing an oxygen bridge rearrange readily to thiolo isomers under tertiary amine catalysis, and all of the thionoanhydrides undergo (4 + 2) cycloadditions with norbornylene.In addition, other α-thiono-substituted naphthalenes have been probed in the norbornylene addition reaction, and some observations have been made concerning the mechanism of the Pedersen thionation reaction.