Tetrahedron Letters p. 4585 - 4588 (1990)
Update date:2022-08-05
Topics:
Gollnick, Klaus
Weber, Maria
Oxygenations of highly strained 1-phenyl- (5a) and 1-(p-tolyl)-substituted 2,2-dimethylbicyclo<1.1.0>butanes (5b), photosensitized by 9,10-dicyanoanthracene in acetonitrile, yield about 90 percent of 1-phenyl- (6a) and 1-(p-tolyl)-substituted 3,4-epoxy-4-methyl-1-pentanones (6b), and about 10 percent of 3-phenyl- (7a) and 3-(p-tolyl)-substituted 3,4-epoxy-4-methylpentanals (7b), respectively.Evidence is presented that ketones 6a,b are formed by an electron-transfer induced process, whereas aldehydes 7a,b are generated by a singlet-oxygen reaction.
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