Enamine chemistry. Part VIII. Reaction of acryloyl chloride with dienamines

Abstract

Reaction of acryloyl chloride with dienamines derived from 3-alkyl-5,5-dimethylcyclohex-2-enones gives mainly the corresponding 6-alkyl-8,8-dimethylbicyclo[3,3,1]non-6-ene-2,9-diones formed by initial carbon–carbon bond formation at the β-position (C-2) and cyclisation at C-6. A tricyclic compound formed by reaction at the β-and δ-positions was also isolated in one case, but in very low yield. Reaction of acryloyl chloride with acyclic linear and cross-conjugated dienamines gives mainly the corresponding 2-alkyl-4-alkenyl- and 2-alkenyl-4-alkyl-3-morpholinocyclohex-2-enones respectively.