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The Ozonolysis of Haloalkenes in Solution
Author(s) -
Gillies Charles W.,
Kuczkowski Robert L.
Publication year - 1983
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198300065
Subject(s) - ozonolysis , chemistry , yield (engineering) , stereoselectivity , reaction mechanism , organic chemistry , mechanism (biology) , computational chemistry , photochemistry , catalysis , thermodynamics , philosophy , physics , epistemology
A review of the ozonolysis of low molecular weight haloalkenes in solution is presented. The reaction products from the fluoroethylene series are discussed in detail. Secondary ozonides can be obtained from these alkenes although the yields decrease markedly with increased fluorination and diminish to negligible quantities with C 2 F 4 . Compared to alkylethylenes, a greater variety of products are obtained including some epoxides and fluorocyclopropanes. Yield data are supplemented by isotopic labeling results to elucidate the ozonolysis mechanism. The evidence indicates that the final ozonides are formed by the three step Criegee reaction mechanism although the stereoselectivity of the reaction differs from nonhaloalkenes.