The Journal of Organic Chemistry

Regioselective functionalization. 5. Nitrogen insertion reactions of bicyclo [3.2. 1] octan-2-one. Reexamination of bridgehead vs. methylene migratory preferences

GR Krow, S Szczepanski

Index: Krow, Grant R.; Szczepanski, Steven Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1153 - 1156

Full Text: HTML

Citation Number: 6

Abstract

Earlier reports of totally regioselective bridgehead nitrogen insertion upon rearrangement of the oxime of bicyclo [3.2. 1] octan-2-one (11, by using benzenesulfonyl chloride/sodium hydroxide as a Beckmann catalyst, but completely regioselective methylene migration upon reaction of ketone 1 with hydroxylamine hydrogen sulfate in sulfuric acid have been found to be inaccurate. Lactams 3, formed by bridgehead migration, and 4, arising from methylene ...