MECHANISM OF ELECTROPHILIC SUBSTITUTION OF FERROCENES
Abstract
Two mechanisms by which metallocenes undergo electrophilic substitution will be considered. The first, exocyclic attack of the electrophilic reagent upon the formally unsaturated rings, is in principle a mechanism analogous to that pertaining to benzenoid systems. The second mechanism invokes the metal atom itself as the initial site of electrophilic attack. Subsequent rearrangement of this intermediate, involving encocyclic attack, leads eventually to the substituted ferrocene. Attempts were made to distinguish between these two courses of reaction by conducting acylation reactions on a series of bridged ferrocenes which offered varying degrees of steric occlusion at the metal atom. Vapor phase analysis of the acyl isomers formed in the course of AlCl3 catalyzed i-butyrylation of ferrocene gave the data for the ratio of 3 to 2 substitution. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 24, 1962
- Accession Number
- AD0289022
Entities
People
- Myron Rosenblum
Organizations
- Brandeis University