Norbornadiene as a Universal Substrate for Organic and Petrochemical Synthesis

V.R. Flid, O.S. Manulik, D.V. Dmitriev, V.B. Kouznetsov, E.M. Evstigneeva,

A.P. Belov and A.A. Grigor’ev

Lomonosov State Academy of Fine Chemical Technology, pr. Vernadskogo 86, Moscow, 117571 Russia

Abstract

A wide range of rare polycyclic hydrocarbons can be obtained through catalytic processes involving norbornadiene (NBD). The problem of selectivity is crucial for such reactions. The feasibility of controlling selectivity and reaction rate has been shown for cyclic dimerization, co-dimerization, isomerization and allylation of NBD. Kinetic rules have been scrutinized. Consistent mechanisms have been proposed. Factors affecting directions of the reactions and allowing us to obtain individual stereoisomers quantitatively have been established. A series of novel unsaturated compounds has been synthesized; they incorporate a set of double bonds with different reactivity and can find an extremely wide range of applications.