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Published August 1, 1959 | public
Journal Article

Small-ring Compounds. XXIII. The Nature of the Intermediates in Carbonium Ion-type Interconversion Reactions of Cyclopropylcarbinyl, Cyclobutyl and Allylcarbinyl Derivatives


Investigation of the extent of isotope-position rearrangement in carbonium ion-type reactions of ^(14)C-labeled cyclopropylcarbinyl derivatives has revealed that the three methylene groups of the starting material achieve a striking degree of equivalence between reactants and products. These results, taken in conjunction with the abnormally large solvolytic reactivities of cyclopropylcarbinyl and cyclobutyl halides and sulfonate esters, can best be accounted for by assuming rapid but not instantaneous equilibration of three isomeric non-classical unsymmetrical "bicyclobutonium" ion intermediates.

Additional Information

© 1959 American Chemical Society. Received September 4, 1958. Supported in part by the Petroleum Research Fund of the American Chemical Society and the U. S. Atomic Energy Commission. Grateful acknowledgment is hereby made to the Donors of the Petroleum Research Fund. Presented in part at the 75th Anniversary Meeting of the American Chemical Society, September 7, 1951; National Research Council Postdoctoral Fellow, 1953-1954; National Science Foundation Predoctoral Fellow, 1955-1958.

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