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. https://resolver.caltech.edu/CaltechAUTHORS:20151001-104318621
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Abstract
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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| Issue or Number: | 9 | |||||||||
| DOI: | 10.1021/ja01177a031 | |||||||||
| Record Number: | CaltechAUTHORS:20151001-104318621 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151001-104318621 | |||||||||
| 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 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | George Porter | |||||||||
| Deposited On: | 13 Oct 2015 21:43 | |||||||||
| Last Modified: | 10 Nov 2021 22:37 |
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