Peer-Reviewed Journal Details
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Cunningham, D,Grayson, DH,McArdle, P,Walsh, JJ
2003
May
Tetrahedron-Asymmetry
The bromination of (-)-camphorquinone
Published
()
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14
1197
1200
The reaction of (-)-camphorquinone with excess moist bromine gives (-)-(1S,5S)-1-bromomethyl-3,3-dibromo-8,8-dimethyl-7-oxabicyclo[3.2.1]octane-2,6-dione rather than 1-bromomethyl-3,5-dibromo-8,8-dimethyl-7-oxabicyclo[3.2.1]octane-2,6-dione as has been reported in the literature. The controlled reaction of moist bromine with (-)-camphorquinone leads to (-)-(1S,5S)-3,3-dibromo-1,8,8-trimethyl-7-oxabicyclo[3.2.1]octane-2,6-dione and not to 5-bromo-l-bromomethyl-8,8-dimethyl-7-oxabicyclo[3.2.1]octane-2,6-dione. (C) 2003 Elsevier Science Ltd. All rights reserved.
DOI 10.1016/S0957-4166(03)00090-9
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