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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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J. M. Birchall, G. N. Gilmore, and R. N. S. Perkin I, 1974, 2530. A. G. Brook, Accounts Chem. , 1974, 7, 77. G. E. Just and C. S. P. 3776940, 3776941 (Chem. , 1974, 80,95363,95364). Three- and Four-membered Rings 37 RRKM theory. -Breslow's group207has attempted to prepare 1,2,3-tribenzoylcyclopropene (148) by the route shown in Scheme 12. The desired product was evidently formed in the reaction mixture, but even when very hindered bases were used for the final dehydrohalogenation step the cyclopropene underwent further, complex changes and could not be isolated.

6463;F. C. D e Schryver, J. Put, L. Leenders, and H. , p. 6994;R. Fleming, F. H. Quina, and G. S. , p. 7738;K Golankiewicz and B. 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.

W. Rees, and R. C. S. Perkin I, 1974, 1260;see also D. S. -S. Lee, and H. W. Moore, J. Org. , 1974,39, 1362. T. Kametani, Japan Kokai, 74 10550 (Chem. A h . 974,80, 145894). 314 1-Benzothiepin (281), obtained from (282) by the action of a rhodium catalyst, has been cyclized photochemically to the cyclobutene (283), which can also be obtained directly from (282) by the action of heat, silver perchlorate, or radiation. For the thermal conversion of (282) into (283), deuterium-labelling studies ruled out an intermediate of type (284), in which rotation of the four-membered ring could occur, and the most likely mechanism appears to be a L2a ,2,] ring-opening to (281a) followed by a conrotatory electrocyclic closure of the latter to (283).

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