Premium
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.