Abstract
The mechanism of deuterium
exchange in the short-chain alkylbenzenes has been
studied using a homogeneous sodium tetrachloroplatinate
catalyst in acetic acid solution. Carbon-14 labelled ethylbenzene
has been synthesized and used to differentiate between previously proposed
mechanisms. When deuteration of the side chain in ethylbenzene occurs, there is no scrambling of the α
and β carbon atoms, thus eliminating the role of a symmetrically
coordinated ethylene group previously proposed. This conclusion is confirmed by
theoretical calculations of the exchange in ethylbenzene.
The ethyl group in ethylbenzene derivatives deuterates with a low multiple character. These results
from the homogeneous platinum system have been compared with corresponding data
using heterogeneous platinum and nickel catalysts. Analogous intermediates are
shown to be capable of existing in both homogeneous and heterogeneous systems,
and are postulated to be general π-complexes for aromatic deuteration and π-allylic
species for alkyl group exchange.
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26 articles.
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