Some reactions of enamines. Part II. Some alkylation reactions of the pyrrolidine enamines of 3,4-dihydronaphthalen-1(2H)-one and 6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one

Abstract

The pyrrolidine enamines (III) and (IV) of 3,4-dihydronaphthalen-1(2H)-one (I) and 6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (II), respectively, were prepared. Alkylation of (III) and (IV) with methyl iodide and with methyl vinyl ketone yielded the α-3-methyl and the α-(3-oxobutyl) ketones of (I) and (II). Conformations for the tricyclic products formed in the intramolecular aldol condensations of the α-(3-oxobutyl) ketones of (I) and (II) are proposed.