Mild one-step synthesis of dibromo compounds from cyclic ethers.

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.

Citation

Peter Billing, Udo H Brinker. Mild one-step synthesis of dibromo compounds from cyclic ethers. The Journal of organic chemistry. 2012 Dec 21;77(24):11227-31

PMID: 23151041

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