Unexpected Formation of 10-Iodo- and 10-Chlorocamphor under Halosulfonylation Conditions, and Convenient Routes to 10-Chloro- and 10-Bromocamphor

Lewis, Frank, Egron, Gilles and Grayson, David (2009) Unexpected Formation of 10-Iodo- and 10-Chlorocamphor under Halosulfonylation Conditions, and Convenient Routes to 10-Chloro- and 10-Bromocamphor. Tetrahedron: Asymmetry, 20 (13). pp. 1531-1535. ISSN 0957-4166

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Abstract

The generation of camphor-10-sulfonyl iodide in situ under halosulfonylation conditions or exposure of camphor-10-sulfonyl chloride to copper(II) chloride under Asscher–Vofsi conditions leads unexpectedly to the formation of 10-iodocamphor or 10-chlorocamphor, respectively. Additionally, convenient syntheses of 10-bromocamphor and 10-chlorocamphor have been achieved by extension of a previously reported methodology.

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