Abstract:
The influence of steric and electronic factors on the reactivity and the stereochemical outcome of epoxidation of cycloalkenes and prochiral alkenes by alkyl hydroperoxides, peroxy acids, oxaziridines, dioxiranes and dimethyl-α-peroxy lactone is analysed comparatively and generalised. The distinctive features of the directing influence of functional groups on the stereochemistry of the epoxide ring closure in the series of ionic, radical and molecular reactions are demonstrated. Some variants alternative to known reaction mechanisms are proposed. The bibliography includes 114 references.
Received: 05.01.1998
Bibliographic databases:
Document Type:
Article
UDC:
547.222.127
Language: English
Original paper language: Russian
Citation:
V. G. Dryuk, V. G. Kartsev, “Mechanism of the directing influence of functional groups and the geometry of reactant molecules on peroxide epoxidation of alkenes”, Usp. Khim., 68:3 (1999), 206–226; Russian Chem. Reviews, 68:3 (1999), 183–201
Linking options:
https://www.mathnet.ru/eng/rcr1453
https://doi.org/10.1070/RC1999v068n03ABEH000398
https://www.mathnet.ru/eng/rcr/v68/i3/p206
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