S H2 reactions of diphenyl diselenide; preparation and reactions of bridgehead selenides

1 January 1981

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications

No. 3,p. 139-140
https://doi.org/10.1039/c39810000139

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.

Keywords

ADAMANTYL
BICYCLO
DISPLACEMENT AFFORDS
DIPHENYL DISELENIDE
RESULTANT SELENOXIDE
PRIMARY ALKYL
H2 REACTIONS
SH2 PROCESS

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