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Accueil > Publications > Recherche par années > Années 1990 > 1991

Bastard, J ; Khac, DD ; Fetizon, M ; Prevost, C ; Beloeil, JC

Mechanism of the rearrangement of the bicyclo[4.2.3]octan system to the bicyclo[3.2.1]octan system

Tetrahedron 47 (2) 229-238

par Administrateur - publié le

Abstract :

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.