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Structural studies of bridgehead alkenes. The x-ray crystal structure of 3-oxabicyclo[5.3.1]deca-1(10)7,(8)-(ZZ)-diene-10-carboxylic acid

✍ Scribed by K.J. Shea; David K. Cooper; W.P. England; Joseph W. Ziller; Timothy G. Lease

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 269 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97186-7

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✦ Synopsis

TheX -ray crystal structure of 3-oxnbicyclo[53.Il&ca-I(1O).7(8)-(zz)-diene-IO-carboxylic acid, a highly strained bridgehead diem?, is reported.

Bridgehead alkenes (1) comprise a subclass of trarrscycloallcenes ( 2), compounds that contain a distorted carbon-carbon double bond.' The magnitude of the distortion increases as the trans-cycloalkene ring size decreases. Despite considerable theoretical interest in these compounds,* there are few structural studies documenting the geometric distortions. 334 We report the X-ray crystal structure of bridgehead diene 3. a compound containing two distorted bridgehead double bonds. Compound 3 constitutes the most highly strained

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