Tetrahedron p. 2111 - 2114 (1981)
Update date:2022-09-26
Topics:
Martinez-Utrilla, R.
Miranda, M. A.
The photochemistry of 5-phenyl-, 5-(2',5'-dimethoxyphenyl)-, 5-(2'-acetoxy-5'-methoxyphenyl)- and 5-(2',5'-diacetoxyphenyl)-2(3H)-furanone (1a-d) has been investigated.Compound 1a yields pheny vinyl ketone as expected.Similarly, 1b affords the corresponding aryl vinyl ketone but, in this case, photodimerization also occurs.Irradiation of the two o-acetoxyaryl furanones 1c and 1d gives rise to the formation of chromones as the main products.This interesting result can be accounted for in terms of a photochemical opening of the lactonic ring followed by radical addition to the acetoxy group.
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Doi:10.1021/ol203140n
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(1981)
