3-Methylene-2-ferrocenylmethylenequinuclidine in cycloaddition and dimerization reactions

Article abstract of DOI:10.1016/S0022-328X(96)06796-4

Cycloaddition, cyclodimerization, and cationic dimerization reactions of 3-methylene-2-ferrocenylmethylenequinuclidine as a ferrocenyl substituted 1,3-diene possessing a fixed s-cissoidal conformation of the double bond system have been investigated. This prepared diene has been shown to form Diels-Alder adducts with azodicarboxylic and/or maleic acid N-phenylimides. It has been shown also that the diene undergoes thermal [4 + 2]-cyclodimerization and links 3-methyl-2,5-(1-pipyridinium-1,4-diyl)-1-ferrocenylallylic cation. The latter reaction results in formation of an adduct of chain structure. The products of alkylation of N,N-dimethylaniline with the intermediate allylic cation have been isolated and characterized for the first time.