Alicyclic Chemistry: Volume 4: A Review of Chemical by Royal Society of Chemistry, W. Parker, Parker W

By Royal Society of Chemistry, W. Parker, Parker W

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43 Three- and Four-membered Rings formed in preference to cyclopentanes. This has been adapted into a general synthesis of functionalized cyclobutanes, and is illustrated by the preparation of ( f)-grandis01 (Scheme 16). 226 Treatment of the tosylate (174) with methanolic potash gives either the cyclobutyl ether (175; X = OMe) or cyclohexenone (176), depending on the reaction times. u. The biradical suffers a combination of fragmentation to styrene and ring ratio (k,) of 10 and a closure to 1,2-diphenylcyclobutanes,with a kc,eavaoe/krotation kcyc,ization/krotation ratio (kB) of 14.

I. T. Jacobson, Chem. Srripta, 1974, 5,227. T. Gibson, J. Org. , 1974,39, 845. M. Christ1 and G. Bruntrup, Chem. , 1974,107,3908. 280 Methylenecyclobutanes are readily obtained by the condensation of an olefin with an allene. Thus, reaction of (221) with acrylonitrile gives (222) and the cyclohexenes (223), the latter resulting from prior rearrangement of (221) to 2-chlorobuta1,3-diene followed by Diels-Alder reaction with acrylonitrile. Compound (222) cyclizes on dehydrochlorination to the unstable 3-methylenebicyclo[2,l,O]pentane (224).

H. Levin, and M. , p. 3575. R. T. Luibrand and R. W. Hoffman, J. Org. , 1974,39,3887. L. Lombard0 and D. Wege, Tetrahedron, 1974,30,3945. 5 kcal mol-'. Wynberg3' has reported three syntheses of spiro[3,3] hepta- 1,5-diene (294),which are summarized in Scheme 23. This chiral hydrocarbon has been resolved uia diastere324 325 D N. C. Yang, R. V. Carr, E. Li, J. K. McVey, and S. A. Rice, J. Amer. Chem. ,1974,96,2297. L. A. Hulshof and H. Wynberg, J. Amer. Chem. Soc.. 1974,96,2191.

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