Published September 1949
| public
Journal Article
The Chlorination of Bicyclo [2,2,1] heptane (Norbornylane)
- Creators
- Roberts, John D.
- Urbanek, L.
- Armstrong, Rose
Chicago
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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).
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.Additional details
- Eprint ID
- 60686
- Resolver ID
- CaltechAUTHORS:20151001-104318621
- National Research Council
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