Magnesium Boryl Reactivity with 9‐BBN and Ph 3 B: Rational B−B′ Bond Formation and Diborane Isomerization | Zendy

Pécharman AnneFrédérique | Zendy; Hill Michael S. | Zendy; McMullin Claire L. | Zendy; Mahon Mary F. | Zendy

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Magnesium Boryl Reactivity with 9‐BBN and Ph 3 B: Rational B−B′ Bond Formation and Diborane Isomerization

Author(s) -

Pécharman AnneFrédérique,

Hill Michael S.,

McMullin Claire L.,

Mahon Mary F.

Publication year - 2017

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201709902

Subject(s) - chemistry , diborane , isomerization , nucleophile , electrophile , medicinal chemistry , reactivity (psychology) , derivative (finance) , double bond , stereochemistry , organic chemistry , boron , catalysis , medicine , alternative medicine , pathology , financial economics , economics

Reactions of a magnesium‐based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9‐BBN and Ph 3 B, provide facile B−B′ single bond formation. Although the Ph 3 B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9‐BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn‐diboration of the resultant alkenyl carbocycle.

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