Steric Effects in Elimination Reactions. IV. The Question of Rearrangements as a Factor in the Extent and Direction of Unimolecular Elimination

HC Brown, Y Okamoto

Index: Brown; Okamoto Journal of the American Chemical Society, 1955 , vol. 77, p. 3619,3621, 3623

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Citation Number: 7

Abstract

The solvolysis of 2-chloro-2, 3, 3-trimethylpentane in 80% aqueous ethanol forms pure 2, 3, 3-trimethyl-l-pentene in 58% yield. The mixture of alcohol and ethyl ether in the solvolysis is converted by hydrogen chloride into a tertiary chloride with identical properties with the original material. In 80% acetone the solvolysis proceeds to give the pure olefin (50% yield) and pure 2, 3, 3-trimethyl-2-pentanol (20% yield). The solvolysis of 3-chloro-2, 2, 3- ...