Abstract
Five N-substituted derivatives of 1,2-methylene-3,4-aziridino 2-phenylsulfonyl cycloalkanes ( 3a-e) were prepared from their corresponding epoxy cyclopropanes via ring opening of the epoxide by sodium azide and subsequent triphenylphosphine induced cyclization. BF 3-induced reaction of compounds 3a-e resulted in a rearrangement via a cyclopropyl carbinyl cation intermediate. In the case of tosylaziridine 3c bicyclic product 5, (tropane skeleton), was formed as the major product. With carbamate derivative 3a exclusive rearrangement to fluorocyloheptene 7 took place.
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