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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
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Publication Date:
31 December 2000 (online)

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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 SH2 reaction of the carbon radical on the disulfide.

SH2 reaction - [bis(1-adamantanecarboxy)iodo]arene - disulfide - adamantyl sulfide - adamantyl selenide