Solvent Effect in Reaction of Singlet Oxygen with Conjugated Dienes

References

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• Denny , R. W. and Nickon , A. 1973 . Organic Reactions , Vol. 20 , 133 New York , N.Y. : John Wiley & Sons . The olefins having β values less than 1.0 can generally be photooxygenated within several hours, whereas those having β values between 1 and 10 may require irradiation of 1 or 2 days as well as addition of radical inhibitors:
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• The photooxygenation was carried out at 4–5°C by means of sodium vapor lamps (National SOI-60, 60W × 8). As a sensitizer, Rose Bengal (4.4 × 10−4M) was used in ethanol and methyl ethyl ketone (MEK), and tetraphenylporphine (1.16 × 10−4M) was used in CHC13, benzene and CCl4. To determine the β values, the consumed oxygen was measured volumetrically.
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• All the endoperoxides obtained here gave satisfactory analytical and spectral data.
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• Matsumoto , M. and Kondo , K. 1975 . ibid. , : 3935
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• It is thought that the reaction proceeds through a 1:l peroxide 12 and the first addition of 1O2 is the rate determining step. Thus β values measured here for the reaction (3) show apparent efficiency in the oxygenation.
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