Pyrolytic Eliminations from N,N-Dichloro Derivatives of Primary, Secondary, and Tertiary Alkyl Primary Amines

Article abstract of DOI:10.1021/jo00334a001

N,N-Dichloro derivatives of primary, secondary, and tertiary alkyl primary amines are easily converted to elimination products by neat or solution pyrolysis during GLC at 190-280 deg C.Good to excellent yields result.In general, the type of product formed depends on the alkyl group: with primary alkyl, the products are alkenes and nitriles; with secondary, alkenes and chloroimines result; and with tertiary types, alkenes are formed.Mechanistic aspects are treated.