Small-Ring Compounds. XLI. The Formolysis of Allylcarbinyl Tosylate

Allylcarbinyl tosylate was found to solvolyze in 98% formic acid 3.7 times faster than n-butyl tosylate. Changes in the rate ratio with nucleophilicity 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 indicated complete scrambling of the methylene groups in the ring-closed products. The results are interpreted in terms of formation of bicyclobutonium ion intermediates.