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Photochemical synthesis of a 2,5-dioxabicyclo [2.2.0] hexane

✍ Scribed by J.Christopher Dalton; Samuel J. Tremont

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 196 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)87101-x

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✦ Synopsis

We report that irradiation of 3-methyl-4-oxa-5-hexen-2-one, 1,, yields al,&dimethyl-2,5-dioxabicyclo[2.2.O]hexane, 2, the first 2,5-dicxabicycLo[2.2.0]hexane to be reported.' 1, was prepared in 39s yield2 by a transetherification reactions between 3hydroxy-2-butanone and methyl vinyl ether (eqn. 1). The structure of 1 is based on the following data: nmr (60 MHz, CC14, 6) 1.3 (3 H, d, J = 7 Hz), 2.1 (3 H, s), 4.03 (3 H, m), 6.3 (1 H, m); ir (Ccl*) 1709 and 1626 cm-'; m/e (rel intensity) 114 (M+, 34), 71 (49), 45 (94), 43 (100); calcd for C6H1002: C

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