Singlet oxygen selective addition

It has already been mentioned (Section III) that the study of the diastereoselection in the electrophilic addition of singlet oxygen to the n face of chiral alkenes is of primary interest for the achievement of a selective oxyfunctionalization reaction. Zeolite confinement and cation- 7r interactions might be expected to affect significantly the diastereoselectivity in the photooxygenation of chiral alkenes. 

The addition of O2 (whether or A ) to 138 or 4 has apparently not been studied theoretically although selection rules for singlet oxygen reactions/ interpretation of substituent effects and orbital correlations for homolytic fission and re-formation of the peroxide bond in 9,10-diphenyl-anthracene peroxide and rubrene peroxide have been published. 

Addition to 3,S-cyeloheptadiene-l-oi (1). Photogenerated singlet oxygen (hematoporphyrin hydrochloride, sensitizer) adds to 1 in a stereoselective manner isyn to OH) to give mainly the endoperoxide 2. The reaction of the acetate of 1 is less selective because the acetyl derivative of 3 rearranges readily under both photolytic and thermal conditions to a diepoxide. Under the same conditions the acetyl derivative of 2 is relatively stable. ... 

K2. Keams, D. R., Selection rules for singlet-oxygen reactions. Concerted addition reactions. J. Am. Chem. Soc. 91, 6554-6563 (1969). 

Srivastava, R.B., Misra, R.B. and Joshi, P.C. (1986) Photosensitized generation of singlet oxygen and superoxide radicals by selected dyestuffs, food additives and their metabolites. P/iotofeioc/iem. Photobiophys. 11 129-137. 

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