Enamine chemistry. Part II. Reaction of αβ-unsaturated acid chlorides with dienamines. Preparation of cyclohexeno(2′,1′:6,7)bicyclo[3,3,1]-non-6-ene-2,9-diones
Abstract
Reaction of acryloyl chloride with dienamines derived from Δ1,8a-2-octalones gives mainly the corresponding cyclohexeno(2′,1′:6,7)bicyclo[3,3,1]-non-6-ene-2,9-dione (20—30%), by initial reaction at C-1 and cyclisation at C-3 of the octalone. Small amounts of 1,8- and 4a,8-bridged products were also isolated. The mechanism of the reaction is discussed.