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Published September 1942 | public
Journal Article

Allylic Rearrangements. XIII. Kinetics and Mechanisms of the Conversion of Crotyl and Methylvinylcarbinyl Chlorides to Acetates and Ethyl Ethers

Abstract

Many investigators, notably Hughes, Ingold and collaborator have demonstrated that the mechanisms of nucleophilic replacement reactions at a saturated carbon atom may be classified into three general types. One mechanism, designated as S_N2 is the familiar bimolecular, usually second-order, substitution of an electron-donor such as hydroxide ion, alkoxide ion or acetate ion for the halide or a similar group as in equation (1), the replacement resulting in a complete Walden inversion.

Additional Information

© 1942 American Chemical Society. Received March 24, 1942. Most of the material of this paper was presented before the Organic Division at the St. Louis and Atlantic City meetings of the American Chemical Society, April and September, 1941. [S. Winstein] National Research Fellow at Harvard University, 1939-1940.

Additional details

Created:
August 19, 2023
Modified:
October 24, 2023