R. Matheson, A. Mcculloch, A. Mcinnes
Apr 15, 1977
Citations
0
Influential Citations
6
Citations
Journal
Canadian Journal of Chemistry
Abstract
Direct irradiation (2537 A) of methyl 1,4-diphenyl-1,4-epoxy-1,4-dihydronaphthalene-2-carboxylate (13b) affords methyl 2,4-diphenyl-3-benzoxepine-1-carboxylate (17b) and methyl 1-benzoyl-3-phenylindene-2-carboxylate (19b), while acetone-sensitized irradiation yields chiefly 19b. The latter can be converted to methyl 3-phenylindene-2-carboxylate (21b).Direct irradiation of dimethyl 1,4-diphenyl-1,4-epoxy-1,4-dihydronaphthalene-2,3-dicarboxylate (13a) affords a mixture of dimethyl 2,4-diphenyl-3-benzoxepine-1,5-dicarboxylate (17a), dimethyl 1-benzoyl-3-phenylindene-1,2-dicarboxylate (19a), and dimethyl 1-benzoyl-2-phenylindene-1,3-dicarboxylate (18). The latter two products cleave readily to give dimethyl 3-phenylindene-1,2-dicarboxylate (21a) and dimethyl 2-phenylindene-1,3-dicarboxylate (20) respectively. Sensitized irradiation yields mainly 19a. The formation of 19a and 19b as major products of photorearrangement of 13a and 13b is consistent with a di-π-methane pathway producing methyl 4,6-diphenyl-5-oxa...