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8544261 
Journal Article 
Reactions Related to the Addition of Dichlorocarbene to Norbornylene 
Bergman, E 
1963 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
28 
9 
2210-2215 
English 
Addition of dichlorocarbene to norbornylene at 0° gave a C8H10Cl2 product isomeric with the expected dichlorocyclopropane derivative. The isomer was shown to be 3,4-dichlorobicyclo[3.2.1]octene-2. Similarly, cyclopentene gave a 40% yield of a 1:1 mixture of the normal product, 6,6-dichlorobicyclo [3.1.0] hexane, and its isomer, 2,3-dichlorocyclohexene. The latter was shown to arise from the former during work-up. Addition of dichlorocarbene to cyclohexene and cycloheptene gave only normal (dichlorocyclopropane) products. The order of stability of the adducts described is consistent with strain being the controlling factor. A stable purple carbonium ion was formed by treatment of either dichlorocarbene adduct of cyclopentene with strong Lewis acids. © 1963, American Chemical Society. All rights reserved.