Photocycloaddition using nitrosobenzene

ORGN 315

Steven A. Fleming and Juliet Go. Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602
Photocycloaddition of nitroso compounds with alkenes may lead to azaoxetane intermediates which upon N-O bond cleavage would provide syn or anti amino alcohols depending on the stereochemistry of the alkene. We have found that two cycloadducts result from the irradiation of styrene and nitrosobenzene. One is a five-member ring heterocycle and we believe the other product is the expected azaoxetane. The mechanism for the formation of these products will be discussed. Irradiation of other alkenes in the presence of nitrosobenzene will also be reported.