MECHANISM OF THE REARRANGEMENT OF THE BICYCLO[4.2.3]OCTAN SYSTEM TO THE BICYCLO[3.2.1]OCTAN SYSTEM

A concerted mechanism has been demonstrated for the rearrangement of a tetracyclic ion including a bicyclo [4.2.0] octan system to hibaol, using a selective deuteration on the migrating bond. The stereochemistry of the selectively introduced deuterium was determined by three routes: I) comparison of the high field H-1 NMR spectra of the deuterated and undeuterated compounds, using double irradiation; II) high field H-1 NMR, coupled with molecular mechanics calculations; III) two dimensional homo and heteronuclear NMR.