SH2 reactions of diphenyl diselenide; preparation and reactions of bridgehead selenides

Abstract

For the S_H2 process R·+ PhSeSePh → PhSeR + PhSe·, k=ca. 5 × 10⁷ mol^–1 s^–1 at 80 °C in benzene when R is primary alkyl; with 1-adamantyl radicals this S_H2 displacement affords a route to 1-adamantyl phenyl selenide which, on oxidation and pyrolysis of the resultant selenoxide, gives adamantan-1-ol; in contrast the selenoxide from bicyclo[3.3.1]nonan-1-yl phenyl selenide decomposes via bicyclo[3.3.1]non-l-ene.