John D. Roberts, L. Urbánek, R. Armstrong
Sep 1, 1949
Citations
0
Influential Citations
9
Citations
Journal
Journal of the American Chemical Society
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).