Mild one-step synthesis of dibromo compounds from cyclic ethers.
Peter Billing, Udo H Brinker
文献索引：J. Org. Chem. 77(24) , 11227-31, (2012)
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摘要
A novel one-step method for mildly converting cyclic ethers into dibromo compounds is reported. Alcohols, oximes, aldehydes, and ketones are known to react under Appel or Corey-Fuchs reaction conditions, but apparently these have never been applied to oxetanes or larger cyclic ethers. Treatment of 3,3-dimethyloxetane (1) with tetrabromomethane and triphenylphosphine gave the corresponding dibromo compound 1,3-dibromo-2,2-dimethylpropane (2). The less-strained homologue oxolane (6) was also reacted giving 1,4-dibromobutane (7) in a 93% yield. Mechanistic interpretations are offered to explain the observed reaction rates of the conversions described.
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Cyclic oligomers in the cationic polymerization of 3, 3-dimethyloxetane. Bucquoye M and Goethals EJ.
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