3-METHYLENE-2-FERROCENYLMETHYLENEQUINUCLIDINE IN CYCLOADDITION AND DIMERIZATION REACTIONS

Cycloaddition, cyclodimerization, and cationic dimerization reactions of 3-methylene-2-ferrocenylmethylenequinuclidine as a ferrocenyl subst ituted 1,3-diene possessing a fixed s-cissoidal conformation of the do uble bond system have been investigated. This prepared diene has been shown to form Diels-Alder adducts with azodicarboxylic and/or maleic a cid N-phenylimides. It has been shown also that the diene undergoes th ermal [4 + 2]-cyclodimerization and links -2,5-(1-pipyridinium-1,4-diy l)-1-ferrocenylallylic cation. The latter reaction results in formatio n of an adduct of chain structure. The products of alkylation of N,N-d imethylaniline with the intermediate allylic cation have been isolated and characterized for the first time.