Conclusions1.Bromination of i-isopropyl-9-borabicyclo[3.3.1]nonane proceeds as a radical process of substitution of the α-hydrogen atom in the isopropyl group, or with splitting of the B-Ci-Pr bond by an eleetrophilic mechanism; any one of these paths predominates, depending on the conditions.2.The formation of sec-alkyl bromides during bromination of sec-alkylborabicyclo[3.3. 1]nonanes proceeds as the result of an electrophilic halodeborylation, and not via the formation ofα-bromoalkylboranes and their proteolysis by the HBr thus liberated.

Bromination of 9-isopropyl-9-borabicyclo[3.3.1]nonane can occur through radical substitution or eleetrophilic mechanism, with sec-alkyl bromides formed through electrophilic halodeborylation.

Paper

Organoboron compounds. Communication 422. Problem of bromination of 9-isopropyl-9-borabicyclo[3.3.1]nonane

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