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The tricyclo[5.3.0.0.3,4]dec-1-ene system

✍ Scribed by R.L. Cargill; A.B. Sears

Publisher: Elsevier Science
Year: 1972
Tongue: French
Weight: 122 KB
Volume: 13
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)94098-5

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✦ Synopsis

Bicyclo[3.2.O]hept-l(7)-ene and compounds containing this highly strained system have remained fugutive,2 although related compounds have been prepared. 2-5 The apparent instability of this system presumably arises from the twist imposed upon the double bond by the trimethylene bridge. When both bridgehead carbons are trigonal, however, the entire molecule may assume planarity with consequent relief of this torsional strain.5 Here we describe the synthesis of compounds which contain the bicyclo[3.2.O]hept-l(7)-ene moiety. Irradiation of 1, $iH 307 nm (E 210), in pentane (Corex) led to no significant change in the gas chromatogram of the irradiation mixture.

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