Reactions of enamines from trans-decalin-2-ones with β-nitrostyrene and phenyl vinyl ketone, and X-ray analysis of 2-p-bromophenyl-4a,5,5a,6,7,8,9,9a,10,10a-decahydro-5a-methyl-10a-morpholino-4H-naphtho[2,3-b]pyran

Abstract

Only the Δ²-isomers of the morpholine enamines from trans-decalin-2-one (1) and 4a-methyl-trans-decalin-2-one (9) react with β-nitrostyrene and phenyl vinyl ketone to give the enaminic adducts (2) and (13), and the naphthopyran derivatives (5) and (16a), respectively. The structures of the products (2), (5), and (13) were assigned from spectral data and their hydrolysis products, while that of (16a) was made through X-ray analysis. The enamine (9) displays reduced reactivity with respect to enamine (1) in the foregoing reactions.