Journal of Organic Chemistry p. 2189 - 2195 (1980)
Update date:2022-07-30
Topics:
Becker, Hans-Dieter
Ruge, Bernd
A series of spirooxirano-substituted bicyclo<2,2,2>octadienons have been prepared by Diels-Alder addition of dimethyl acetylenedicarboxylate to 2,4-cyclohexadienones, and their photochemistry was investigated.Upon direct exitation, they were found to aromatize by elimination of 2-carbonyloxirane which was trapped by ethanol to give ethyl glycidate.The acetophenone-sensitized reaction of bicyclooctadienones gave tricyclic isomeres whose formation by regiospecific di-?-methane rearrangement is discussed.
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Doi:10.1021/jo01046a533
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(1983)
