The reaction of trichlorosilane with enamines

A previously unknown reaction of trichlorosilane with enamines has been discovered and a preliminary study done on the possible mechanism. The products of the reaction are a regiospecific trichlorosilyl adduct resulting from addition of the trichlorosilane to the enamine unsaturation and the amine corresponding to simple reduction of the double bond. The addition of the trichlorosilane requires no catalyst and the relative percentages of the products varies in a generally inverse fashion depending on the exact structure of the enamine. Evidence is given to support the assigned structure of the trichlorosilyl species and mechanisms are hypothesized to explain the formation of both products from a common intermediate. Steric rather than electronic factors are suggested as responsible for the observed balance between them.