Accession Number : AD0426962


Title :   SMALL-RING COMPOUNDS. XLI. THE FORMOLYSIS OF ALLYLCARBINYL TOSYLATE,


Corporate Author : CALIFORNIA INST OF TECH PASADENA GATES AND CRELLIN LABS OF CHEMISTRY


Personal Author(s) : Servis,Kenneth L ; Roberts,John D


Report Date : Dec 1963


Pagination or Media Count : 18


Abstract : Allylcarbinyl tosylate was found to solvolyze in 98% formic acid 3.7 times faster than n-butyl tosylate. Changes in the rate ratio with nucle ophilicity of the solvent suggests different mechanisms for these solvolyses. The formolysis products of allylcarbinyl tosylate were found to be virtually identical with those from cyclobutyl tosylate. Deuterium labeling experiments indi cated complete scrambling ofe3e methylene groups in the ring-closed products. The results are interpreted in terms of formation of bicyclobu tonium ion intermediates. (Author)


Descriptors :   SOLVATION , SOLVATION , NUCLEAR PROPERTIES , CYCLOALKANES , DEUTERONS


Distribution Statement : APPROVED FOR PUBLIC RELEASE