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Deboronation and Deprotonation of ortho ‐Carborane with N‐Heterocyclic Carbenes
Author(s) -
Willans Charlotte E.,
Kilner Colin A.,
Fox Mark A.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001730
Subject(s) - carbene , carborane , deprotonation , steric effects , adduct , chemistry , yield (engineering) , medicinal chemistry , boron , alkyl , ion , stereochemistry , organic chemistry , materials science , catalysis , metallurgy
It is a matter of size : N‐Heterocyclic carbenes can remove a proton from ortho ‐carborane to form a two‐cage anion or attack the electropositive boron of ortho ‐carborane to yield a stable 1:2 carborane–carbene adduct. Which end product is formed depends on the steric bulk of the alkyl groups attached to the nitrogen atoms of the carbene.