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The Chlorination of Bicyclo [2,2,1] heptane (Norbornylane)

Roberts, John D. and Urbanek, L. and Armstrong, Rose (1949) The Chlorination of Bicyclo [2,2,1] heptane (Norbornylane). Journal of the American Chemical Society, 71 (9). pp. 3049-3051. ISSN 0002-7863. doi:10.1021/ja01177a031.

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The nitration of bicyclo [2,2,1]heptane (norbornylane) has been reported to give 1-nitrobicyclo[2,2,1]heptane. In the present investigation a study was made of the peroxide-catalyzed chlorination of bicyclo [2,2,1]heptane with sulfuryl chloride in an attempt to find a convenient synthesis for the 1- and 7-chlorobicyclo [2,2,1]-heptanes. Both mono- and dichloro products were isolated from the chlorination of bicyclo-[2,2,1]heptane in methylene chloride solution. The monochloride fraction had practically the same physical properties (Table I) and infrared absorption spectrum (Fig. 1) as a sample of norbornyl chloride (2-chlorobicyclo [2,2,1]heptane) made by the addition of hydrogen chloride to norbornylene (bicyclo [2,2,1]1-heptene).

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Additional Information:© 1949 American Chemical Society. Received October 30, 1948. We are indebted to Dr. R. C. Lord, Jr., and Mr. R. S. McDonald for the infrared determinations. [John D. Roberts] National Research Fellow in Chemistry, Harvard University, 1945-1946.
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National Research CouncilUNSPECIFIED
Issue or Number:9
Record Number:CaltechAUTHORS:20151001-104318621
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Official Citation:The Chlorination of Bicyclo [2,2,1] heptane (Norbornylane) John D. Roberts, L. Urbanek, and Rose. Armstrong Journal of the American Chemical Society 1949 71 (9), 3049-3051 DOI: 10.1021/ja01177a031
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60686
Deposited By: George Porter
Deposited On:13 Oct 2015 21:43
Last Modified:10 Nov 2021 22:37

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