Tetrahedron letters

Pinacol reduction-cum-rearrangement. A re-examination of the reduction of aryl alkyl ketones by zinc–aluminum chloride

AA Grant, M Allukian, AJ Fry

Index: Grant, Anya A.; Allukian, Myron; Fry, Albert J. Tetrahedron Letters, 2002 , vol. 43, # 24 p. 4391 - 4393

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Citation Number: 6

Abstract

We recently had need for a series of symmetrically substituted dialkylstilbenes (2). A report that aryl aldehydes and ketones (1) can be condensed to the corresponding alkenes 2 by a mixture of zinc and aluminum chloride in acetonitrile 1 (Eq. (1)) promised to provide a convenient route to the desired substances. However, we report here that in our hands little or no alkene is formed from aryl alkyl ketones (1). Rather, the reaction takes a quite different course leading ...

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