Journal of the American Chemical Society p. 7373 - 7379 (1979)
Update date:2022-08-05
Topics:
Wilson
Phillips
Pelister
Huffman
Two new syntheses of cyclobutene esters and the use of 1-cyanocyclobutene as potential isoprene synthons are described. Photocycloaddition of methyl cyclobut-1-enecarboxylate and 1-cyanocyclobutene to piperitone, followed by reduction and lactonization, gives photodihydroarisolactone. Single-crystal X-ray analysis of the latter and a related compound reveals interesting structural features in the strained bicyclo left bracket 2. 2. 0 right bracket hexane system. Thermolysis of these lactones yields 1,5-cyclodecadienes related to germacrene sesquiterpenes.
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