Small-ring Compounds. XXIII. The Nature of the Intermediates in Carbonium Ion-type Interconversion Reactions of Cyclopropylcarbinyl, Cyclobutyl and Allylcarbinyl Derivatives1a

Autor:	Marc S. Silver, John D. Roberts, William N. White, C. C. Lee, Robert H. Mazur, Dorothy A. Semenow
Rok vydání:	1959
Předmět:	Halide General Chemistry Ring (chemistry) Photochemistry Biochemistry Catalysis Ion chemistry.chemical_compound Colloid and Surface Chemistry Sulfonate chemistry Carbonium ion Computational chemistry Methylene
Zdroj:	Journal of the American Chemical Society. 81:4390-4398
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja01525a073
Popis:	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.
Databáze:	OpenAIRE
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