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1981•Journal of the Chemical Society Chemical CommunicationsRequires access

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

M. J. Perkins, Eric S. Turner

Open publisher page 35 citations

Abstract

For the SH2 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 SH2 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.

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What this paper is about

For the SH2 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 SH2 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.

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OpenAlex reports 35 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

For the SH2 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 SH2 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.

Key concepts: Selenide, Diselenide, Diphenyl diselenide, Chemistry, Benzene, Bicyclic molecule, Radical, Medicinal chemistry

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