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Synlett 2010(5): 774-776  
DOI: 10.1055/s-0029-1219204
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Paracyclophane Thiols via an Unprecedented Reduction-Deprotection Sequence: Direct Conversion of tert-Butyl Sulfoxides into Thiols with Boron Tribromide

Christian Friedmann, Stefan Bräse*
Karlsruhe Institute of Technology, Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)608858; e-Mail: braese@kit.edu;
Further Information

Publication History

Received 1 November 2009
Publication Date:
17 February 2010 (online)

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Abstract

Starting from readily available paracyclophane-substituted sulfoxides, a two-step procedure including a directed ortho-metalation and an unprecedented deoxygenation-deprotection sequence allows the generation of versatile functionalized paracyclophane thiols.

Key words

cyclophanes - sulfoxides - thiols - reduction - deoxygenation

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See also ref. 6b and 6c.