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Lookup NU author(s): Emeritus Professor Bill Clegg
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The remarkably stable crystalline perhydrate 1 derived from alpha-bromocyclohexanone has been characterised by X-ray crystallography providing the first example of a perhydrate crystal structure. Perhydrate 1 exists in alternative chair conformations in chloroform and tetrahydrofuran with the bromine substituent occupying equatorial and axial positions, respectively. The perhydrate 1 can oxidise sulfides to sulfoxides in good yields in dichloromethane but not in tetrahydrofuran. The requirement for bromine to be equatorial for a stable perhydrate to form is demonstrated using conformationally locked cis and trans 2-bromo-4-tert-butylcyclohexanones in which case only the cis isomer 4a forms a perhydrate. (C) 2000 Elsevier Science Ltd. All rights reserved.
Author(s): Carnell AJ, Clegg W, Johnstone RAW, Parsy CC, Sanderson WR
Publication type: Article
Publication status: Published
ISSN (print): 0040-4020
ISSN (electronic): 1464-5416
Publisher: Elsevier Science Ltd.
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