The Reaction of 5-Substituted-2-Norbornenes with Phenylselenyl Chloride

D. Alan R. Happer; Thomas Francis; Jonathan M. White

doi:10.1071/CH08091

RESEARCH ARTICLE

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The Reaction of 5-Substituted-2-Norbornenes with Phenylselenyl Chloride

D. Alan R. Happer ^A ^C , Thomas Francis ^A and Jonathan M. White ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, University of Canterbury, Christchurch 8140, New Zealand.

^B Department of Chemistry, University of Melbourne, Parkville VIC 3010, Australia.

^C Corresponding author. Email: alan.happer@canterbury.ac.nz

Australian Journal of Chemistry 61(4) 283-287 https://doi.org/10.1071/CH08091
Submitted: 4 March 2008 Accepted: 18 March 2008 Published: 24 April 2008

Abstract

In dichloromethane, 5-substituted-2-norbornenes add phenylselenyl chloride across the double bond to give adducts in which the phenylselanyl substituent is exo and the chloro endo. The relative yields of the two regioisomeric adducts are reported for several of these. For most, the formation of the 2-chloro-3-phenyselanyl adduct is favoured. The main exceptions are when the 5-substituent is exo and a good resonance donor, where the 3-chloro-2-phenylselanyl adduct is the major product. Possible factors influencing the product distribution are discussed.

References

The Reaction of 5-Substituted-2-Norbornenes with Phenylselenyl Chloride

Abstract

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