The Journal of Organic Chemistry

Sensitized Photooxygenation of 6-Heteroatom-Substituted Fulvenes: Primary Products and Their Chemical Transformations

X Zhang, F Lin, CS Foote

Index: Zhang, Xiaojun; Lin, Feng; Foote, Christopher S. Journal of Organic Chemistry, 1995 , vol. 60, # 5 p. 1333 - 1338

Full Text: HTML

Citation Number: 12

Abstract

Sensitized photooxygenation of 6, 6-diethoxyfulvene (1) and 6, 6-(ethylenedithio) fulvene (9) at-78" C afforded diethoxyfulvene endoperoxide 2 and (ethy1enedithio) fulvene endoperoxide 10, respectively, as primary products. Further irradiation resulted in formation of the novel bisperoxides 3 and 11 from [2+ 21 cycloaddition of IO2 to the exocyclic double bond of the corresponding endoperoxides. The initial endoperoxides were characterized ...