Carnell AJ

Clegg W

Johnstone RAW

Parsy CC

Sanderson WR

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

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

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