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8348094 
Journal Article 
2-Halo-2-cyclohexenols from 6,6-dihalobicyclo-[3.1.0]hexanes and dimethyl sulfoxide. Studies towards a non-basic hydroxide equivalent 
Wessjohann, LA; Mã¼Hlbauer, A; Sinks, U 
1997 
Yes 
Acta Chemica Scandinavica
ISSN: 0904-213X
EISSN: 1902-3103 
Blackwell Munksgaard 
51 
11 
1112-1115 
English 
A practical, high yielding, cheap and mild method for the synthesis of 2-halo-2-cycloalkenols, especially 2-bromo-2-cyclohexenol, is reported. Direct conversion from a variety of thermally labile n,n-dihalobicyclo[n-3.1.0]alkanes to 2-halo-2-cycloalkenols can be achieved without using silver salts by simple heating in DMSO. The intermediate 1,n-dihalocycloalkenes immediately undergo indirect allylic substitution with DMSO to yield the corresponding halocycloalkenols. A possible mechanism for the substitution step comprises nucleophilic attack by DMSO followed by a Pummerer rearrangement and hydrolytic decomposition. Kinetic and mechanistic experiments to verify the course of the reaction are presented. © Acta Chemica Scandinavica 1997.