Aliphatic, Alicyclic and Saturated Heterocyclic Chemistry

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C . Caserio, SeIectiue Org. , 1970, 1, 239. L. R. Byrd and M. C. Caserio, J . Amer. Chem. ,1970, 92, 5422. Acetylenes, Allenes, and OleJiris 45 products are also obtained. None of the products isolated using optically active penta-2,3-diene are optically active. l4l Addition of hypochlorous acid to allenic hydrocarbons, an electrophilic attack, leads, in all cases, to the placement of the chlorine on the central carbon atom and the OH group on the more substituted of the allenyl ~ a r b 0 n s .

DeVille, J. Hora, M. B. Hursthouse, T. P. Toube, and B. C. L. Weedon, Chem. , 1970, 1231. J. K. Kochi and P. J. Krusic, J . Amer. Chem. ,1970, 92, 4110. R. F. Heck, Fortschr. Chem. , 1971, 16, 221. J. Sicher, Pure Appl. , 1971, 25, 655. A. J. Parker, Chem. , 1971, 297. M. , 1970, 5 , 1. J. Reucroft and P. G. Sammes, Quart. , 1971, 25, 135. J. D. Faulkner, Synthesis, 1971, 175. -Much effort has been expended recently in devising new methods for stereospecific syntheses of substituted ~ l e f i nand, ~ ~in ~ particular, ~ , ~ ~their ~ application to the synthesis of biologically important terpenoids.

R. Dodd, J . Amer. Chem. ,1970,92, 6507. lo8 D. Rosenberg and W. Drenth, Tetrahedron, 1971, 27, 3893. log F. , Chem. , 1971, 104, 11, 954, 958, 961, 1322, 1329, 1362, 1962, 2030, 2354. lo5 lo* R. -A usually reliable method of preparing allenes is by the insertion of cyclopropylidene carbenes (carbenoids). l1° The dibromocyclopropane (155) yields only the bicyclobutane (156) and no allene is detectable, whereas the isomeric dibromocyclopropane (1 57) yields, in addition to the bicyclobutane (158), appreciable amounts of allene (159).

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