Journal of the American Chemical Society

Rearrangement of Alkyl Groups. Kinetic and Tracer Studies in the Pinacol Rearrangement1

M Stiles, RP Mayer

Index: Stiles; Mayer Journal of the American Chemical Society, 1959 , vol. 81, p. 1497,1503

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Citation Number: 73

Abstract

The rearrangement of 2, 3-dimethyl-2, 3-pentanediol (IIb) in aqueous sulfuric acid yielded 83% methyl t-amyl ketone and 17% ethyl t-butyl ketone. Isotopic labeling showed that the methyl ketone arose both by ethyl migration (69%) and methyl migration (31''0). Similar rearrangement of 2, 3, 4, 4-tetramethyl-2, 3-pentanediol(IIc) led to 98.6% methyl triptyl ketone and 1.4'; h hesamethylacetone. In this case the methyl ketone was shown to result ...

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