J. McCullough, Roderick C. Miller, W. Wu
Aug 1, 1977
Citations
0
Influential Citations
28
Citations
Journal
Canadian Journal of Chemistry
Abstract
The photoreactions of 1- and 2-naphthonitriles with tetramethylethylene have been studied in the solvents hexane, benzene, dimethoxyethane, methanol, and acetonitrile. In hexane, benzene, or dimethoxyethane, the exclusive products are the cyclobutanes 1-cyano-7,7,8,8-tetramethyl-2,3-benzobicyclo[4.2.0]octa-2,4-diene (from 1-naphthonitrile and tetramethylethylene), and 6-cyano-7,7,8,8-tetramethyl-2,3-benzobicyclo[4.2.0]octa-2,4-diene (from 2-naphthonitrile). In methanol, products of photoreduction are formed. From 2-naphthonitrile and tetramethylethylene in methanol are obtained 1-(2′-methoxy-1′,1′,2′,2′-tetramethyl)-3-cyano-1,4-dihydronaphthalene, 1-(2′-methoxy-1′,1′,2′,2′-tetramethyl)-2-cyano-2,4-dihydronaphthalene, and l,2-dihydro-2-naphthonitrile. Deuterium incorporation is observed with CH3OD as solvent, and the stereochemistry of solvent incorporation is discussed. Reaction in 2,2,2-trifluoroethanol proceeds similarly. In methanol, 1-naphthonitrile and tetramethylethylene give products of reductive d...