United States Patent Office Patented June 17, 1969
3,450,782 United States Patent Office Patented June 17, 1969 2 1,3-dibromocyclobutane with sodium in refluxing dioxane, 3,450,782 PROCESS FOR THE PREPARATION OF K. B. Wiberg, G. M. Lampman, R. P. Ciula, D. S. Con CYCLICALKANES nor, P. Scherter, and J. Lavanesh, Tetrahedron, 21, 2749 Daniel S. Connor, Cincinnati, Ohio, assignor to The (1695), bicyclo[1.1.1 pentane by treatment of 3-(bromo Procter & Gamble Company, Cincinnati, Ohio, a cor methyl)-cyclobutyl bromide with sodium metal at a 0.5% poration of Ohio yield, with lithium amalgam in refluxing dioxane at a No Drawing. Filed Nov. 29, 1967, Ser. No. 686,738 4.2% yield and with sodium/naphtahalene at a 8% yield, Int, C. C07c I/28 K. B. Wiberg, D. S. Connor, and G. M. Lampman, Tetra U.S. C. 260-666 8 Claims hedron Letters, 531 (1964); K. B. Wiberg and D. S. Con 0 nor, J. Am. Chem. Soc., 88, 4437 (1966). On examination of the literature hereinbefore cited ABSTRACT OF THE DISCLOSURE on cyclization, it is apparent that the yields obtained were This invention concerns the preparation of cyclic al extremely low, that the conditions for reaction when it kanes from dihalogenated alkanes using lithium amalgam. did occur were quite severe, and that the starting materials 5 used were less than common. OBJECTS OF THE INVENTION SUMMARY OF THE INVENTION The use of the method of this invention to obtain cyclic The object of this invention is to prepare cyclic al compounds provides a valuable synthetic tool heretofore kanes from the halogenated straight chain starting ma 20 unknown to chemists, thus enabling the production of terials using lithium amalgam to remove the halogens valuable end products.
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