Journal
TETRAHEDRON
Volume 65, Issue 52, Pages 10856-10862Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.10.086
Keywords
Reduction; SmI2; Birch; Benzyl alcohol; Benzyl amine; Benzyl thiol
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Funding
- Swedish research council
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The SmI2/H2O/pyrrolidine mediated cleavage of benzylic alcohols and benzyl groups was studied and found to be a viable alternative to the Birch reduction yielding the corresponding deoxygenated product in excellent yield. The reaction has been investigated by kinetic methods, and a mechanism involving a pre-complexation of the alcohol to SmI2 followed by an amine mediated electron transfer and subsequent bond cleavage and transfer of a second electron and proton to yield the toluene product has been proposed. The reaction is strongly inhibited at higher concentrations of water, indicating that it proceeds via an inner-sphere electron transfer from samarium(II) to the benzyl group, and excess of water prevents coordination of benzyl alcohol to samarium. (C) 2009 Elsevier Ltd. All rights reserved.
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