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Chemistry of organoborates. Part 4. Stereochemistry and relative migratory aptitudes of alkyl groups in the cyanoborate process

Pelter, Andrew, Hutchings, Michael G., Smith, Keith and Williams, David J. 1975. Chemistry of organoborates. Part 4. Stereochemistry and relative migratory aptitudes of alkyl groups in the cyanoborate process. Journal of the Chemical Society, Perkin Transactions 1 (2) , pp. 145-150. 10.1039/P19750000145

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Abstract

All three possible migrations from boron to carbon in the cyanoborate process involve retention of configuration at the migrating centre. For each of the three migrations the relative migratory aptitudes of alkyl groups are in the order n- > s- > t-a result rationalised in terms of the charge density at carbon in the transition state. Products derived from certain di- and tri-substituted olefins should theoretically be mixtures of diastereoisomers and in one instance this has been verified.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: RSC Publishing
ISSN: 0300-922X
Last Modified: 04 Jun 2017 02:50
URI: http://orca.cf.ac.uk/id/eprint/12580

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