Yields and stereoselectivities of chlorinolysis of ... - ACS Publications

Apr 29, 1988 - Donna J. Nelson* and Raman Soundararajan. Department of Chemistry, University of Oklahoma, Norman, Oklahoma 73019. Received April 29 ...
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J. Org. Chem. 1988,53, 5664-5668

5664

Yields and Stereoselectivities of Chlorinolysis of Trialkylboranes. Comparison of a Variety of Selected Methods Donna J. Nelson* and Raman Soundararajan Department of Chemistry, University of Oklahoma, Norman, Oklahoma 73019

Received April 29, 1988 Yields and stereoselectivitiesfor chlorinolysis of a series of representative trialkylboranes R3B (R = pentyl, hexyl, cyclohexyl, sec-butyl, ezo-2-norbornyl)with a variety of chlorinolysis methods (CuC12/H20;FeC1,; dichloramine T; NCl,; t-BuOC1) are compared. Of the easily handled reagents, dichloramine T generalIy gives good yields and is most stereoselective(>99% exo-:99:99:99: