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Communication | Special issue | Vol 18, No. 1, 1982, pp.163-167
Published online, 1st January, 1970
DOI: 10.3987/S(B)-1982-01-0163
Cleavage of Cyclic Ethers with Boron Bromide. A Convenient Route to the Bromosubstituted Alcohols, Aldehydes and Ketones

Surendra U. Kulkarni* and Vemanna D. Patil

*Wetherill Laboratory, Purdue University, West Lafayette, Indiana 47907, U.S.A.


Cyclic ethers are readily cleaved by BBr3 under mild conditions, providing the corresponding ω-bromoalkylborates (1). Redistribution of 1 with methanol affords ω-bromoalcohols (2). Oxidation of 1 with pyridinium chlorochromate forms the corresponding ω-bromoaldehydes (3). Under these conditions, epoxides yield first the borates of the corresponding bromohydrins, with subsequent oxidation of the intermediate (without isolation), giving the α-bromoketones in high purity and satisfactory yield.