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2-Bromocyclohexanone perhydrat - X-ray crystal structure and conformational effects on reactivity in sulfoxidations

Lookup NU author(s): Professor William Clegg

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Abstract

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.

Publication metadata

Author(s): Carnell AJ, Clegg W, Johnstone RAW, Parsy CC, Sanderson WR

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2000

Volume: 56

Issue: 35

Pages: 6571-6575

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Elsevier Science Ltd.

URL: http://dx.doi.org/10.1016/S0040-4020(00)00608-6

DOI: 10.1016/S0040-4020(00)00608-6

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