Journal of the American Chemical Society

Properties of. alpha.-keto cations. Facile generation under solvolytic conditions

X Creary, CC Geiger

Index: Creary,X.; Geiger,C.C. Journal of the American Chemical Society, 1982 , vol. 104, p. 4151

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Citation Number: 80

Abstract

Abstract: a-Keto mesylates 2-10 have been prepared. In a variety of solvents, they undergo solvolysis under relatively mild conditions. Product and rate data implicate the intermediacy of tertiary a-keto cations in the solvolyses of 2-6 and secondary benzylic a-keto cations in the solvolyses of 7-10. On acetolysis, mesylate 2 gave the Wagner-Meerwein rearrangement product 35 and the product of 1, 3-hydride shift, 34, along with the elimination product, 33. ...

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