Metal catalysis in organic reactions. Part II. Products and stereochemical aspects of the isomerization of heptenes by the tri-isobutyl-aluminium–bis-N-methylsalicylideneaminenickel system

Abstract

The isomerization of some C₇ olefins in the presence of tri-isobutylaluminium–bis-N-methylsalicylideneamine-nickel has been studied. The susceptibility to isomerization of the substrates was found to be related to their structure: in particular 1-olefins were rapidly converted mainly into (E)-2-olefins. Moreover, whereas linear internal olefins were isomerized, branched chain internal olefins were unreactive under the conditions adopted. The isomerization of (S)-4-methylhex-1-ene to (S)-(E)-4-methylhex-2-ene occurred without racemization. The nature of the active species is discussed and reaction paths are suggested.