NDLI: Free-radical reactions of halogenated bridged polycyclic compounds. Part X. Addition of bromine and chlorine to hexachloronorbornadiene

Content Provider	Royal Society of Chemistry (RSC)
Author	Davies, D. I. Parrott, M. J.
Copyright Year	1970
Abstract	The addition of bromine in carbon tetrachloride or acetic acid to hexachloronorbornadiene affords the products of endo-cis- and trans-addition of bromine to the unsubstituted double bond, and the rearrangement product 5-exo,-7-anti-dibromo-1,2,3,5-endo,6,6-hexachloronorborn-2-ene. With chlorine, in addition to the products of endo-cis- and trans-addition, two rearrangement products, 1,2,3,5,5,6,6,7-anti-octachloronorborn-2-ene and its 7-syn-epimer, are formed. The effect of changes in temperature, and of added free-radical catalysts and inhibitors, on the product ratios, has been examined to provide evidence for possible intermediates in these addition reactions. Sulphuryl chloride has been used to add, in a free-radical manner, the elements of chlorine to hexachloronorbornadiene. This affords the products of endo-cis- and trans-addition to the unsubstituted double bond together with the rearrangement product 1,2,3,5,5,6,6,7-anti-octachloronorborn-2-ene.
Starting Page	659
Ending Page	663
Page Count	5
File Format	PDF
ISSN	00224952
Volume Number	0
Issue Number	5
Journal	Journal of the Chemical Society C: Organic
DOI	10.1039/J39700000659
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Bromine Carboxylic acid Chlorine Carbon tetrachloride Double bond
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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Free-radical reactions of halogenated bridged polycyclic compounds. Part X. Addition of bromine and chlorine to hexachloronorbornadiene