Preparation of Adamantyl Sulfides with [Bis(1-adamantanecarboxy)iodo]arenes and Disulfides

Hideo Togo; Takahito Muraki; Masataka Yokoyama

doi:10.1055/s-1995-3877

Synthesis 1995; 1995(2): 155-157
DOI: 10.1055/s-1995-3877

short paper

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Preparation of Adamantyl Sulfides with [Bis(1-adamantanecarboxy)iodo]arenes and Disulfides

Hideo Togo^* , Takahito Muraki, Masataka Yokoyama¹

^*Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263, Japan

Abstract

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Irradiation of [bis(1-adamantanecarboxy)iodo]arenes with a high-pressure mercury lamp in the presence of disulfides gives the corresponding adamantyl sulfides in high yields. This reaction proceeds via the radical decarboxylation of [bis(1-adamantanecarboxy)iodo]arenes followed by S_H2 reaction of the carbon radical on the disulfide.

S_H2 reaction - [bis(1-adamantanecarboxy)iodo]arene - disulfide - adamantyl sulfide - adamantyl selenide

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