Organic letters

Ozonolysis in the presence of Lewis acids: Directed addition to carbonyl oxides

PH Dussault, JM Raible

Index: Dussault, Patrick H.; Raible, Joseph M. Organic Letters, 2000 , vol. 2, # 21 p. 3377 - 3379

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Citation Number: 23

Abstract

Ozonolysis of alkenes is still one of the most popular methods for cleavage of alkenes. 1 The mechanism of this process, elucidated by Criegee more than 50 years ago, consists of dipolar cycloaddition to form a seldom-observed primary ozonide (1,2,3-trioxolane), followed by cycloreversion to carbonyl oxide (CO) and carbonyl fragments (Scheme 1). 2,3 The fate of the short-lived CO is dictated by reaction conditions. Ozonolysis in the presence of protic nucleophiles ...