An experimental and theoretical study of the degenerate carbon skeleton isomerization of the cyclopentyl cation in the gas phase

Franke, Wilfred ; Schwarz, Helmut ; Thies, Helga ; Chandrasekhar, Jayaraman ; Schleyer, Paul von Rague ; Hehre, Warren J. ; Saunders, Martin ; Walker, Gray (1980) An experimental and theoretical study of the degenerate carbon skeleton isomerization of the cyclopentyl cation in the gas phase Angewandte Chemie International Edition, 19 (6). pp. 485-487. ISSN 1433-7851

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.19...

Related URL: http://dx.doi.org/10.1002/anie.198004851

Abstract

The non-classical pyramidal cation(4) provides a rational explanation of all the phenomena observed on mass-spectrometic degradation of the cyclopentyl cation (1). On generation from (2a), (2b), (3a), or (3b) (• = 13C), (1) always gives 13C2H4, 13C12CH4, 12C2H4 in the ratio of 10:60:30, i.e. all the C atoms must have become statistically equivalent prior to elimination of ethylene from (1). MINDO/3 calculations show degradation to proceed via the cations (4) and (5).

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