Abnormal Ozonolysis of Methylenebicyclo[m. n. 1]alkanes

Abstract

Ozonolysis of d-longifolene [1], camphene [9], 8-pinene [17] and 1, 7, 7-trimethy1-2-methylenenorbornane [22] has been carefully examined. On ozonolysis of [1] and [22], abnormal oxidation products were obtained as the principal products. However, oxonolysis of [9] and [17] afforded mainly the corresponding ketones and the Baeyer-Villiger type oxidation products. These results indiacte that the steric hindrance caused by the bulky group at the C-7 position of these bicycloalkane systems is an important factor leading to the abnormal ozonolysis.