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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Skalski Bull. Acad. polon. , Ser. Sci. , 1974,22,395 (Chem. , 1974,81,120569). J. J. Gajewski L. K. Hoffman, and C. N. Shih, J . Amer. Chem. , 1974,%, 3705. J. J. Dannenberg, T. M. Prociv, and C. Hutt, J. Amer. , 1974,96,913. Three- and Four-membered Rings 47 A further, somewhat more efficient route to the propellane is the electrochemical reduction of the dibromide (195; X = Br) at relatively negative electrode potentials. 243 Cyclobutanes have been. synthesized in a routine manner by the p h o t o ~ h e m i c a l and , ~ ~ ~r n e t a l - c a t a l y ~ e ddimerizations ~~~ of olefins.

Three- and Four-membered Rings 49 ethanol, at a rate much faster than either cyclobutane isomer (205; R = Et) opens to (204) in P O E t NC (200) NC NC CN CN WoR OR (203b) NC NC 1 C CN &pN NC CN Use of the methyl ethers (203; R = Me) in ethanol and of the ethyl ethers (203; R = Et) in methanol allows the conformation and reactivity of the intermediate 1,4-dipoles to be examined more closely. The results obtainedz5' indicate that the cis-zwitterion (206a; R = Me) reacts with alcohols 5-8 times than it undergoes cyclization to (205).

280 281 ’’’ S . Farber and R. T. , 1974,4, 243. H. K. Hall, jun. and R. E. Yancy. J. Org. , 1974,39,2862. F. E. Ziepler and J. A. Kloek, Tetrahedron Letters, 1974, 315. ~~~ In the case of l,1-dimethylallene, the 3: 1 ratio of products (232a) and (232b) was found to be constant over the range 80-150°C, indicating that the two isomers are not formed by independent pathways, but via a common biradical(231) in different conformations. )-C= + CF,C-CCF, F3CA 6 , EF3+ (232a) CF3 c@(232b) Photochemical rearrangement of aj3- or flyunsaturated ketones may give rise to methylenecyclobutanols.

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