On the mechanism of ring opening in 2-pyrone irradiations

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Abstract
The irradiation of 2-pyrone in benzene followed by pyrolysis gives a poor yield of cyclooctatetraene. The irradiation of 4-methoxy-6-methyl-2-pyrone in water gives cis-β-methyl glutaconic half ester and the corresponding diacid. Irradiation in benzene followed by the addition of water gives a mixture of the cis and trans glutaconic derivatives. It is believed that these substances derive from the β-lactone formed by irradiation, and support for this view is obtained from low temperature irradiations. An oligomeric intermediate (16) is suggested as a second intermediate in the irradiation in benzene, and a hemiketal (20) in the aqueous irradiation.

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