Boron trifluoride mediated addition of nucleophiles to endo- and exo-substituted norbornene derivatives

Date

2004-01-01

Author

İŞLEYEN, Alper
SAYRAÇ, Tuğmaç
Doğan, Özdemir

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Remote substituent effects on the regioselectivity and stereoselectivity in the boron trifluoride mediated addition of nucleophiles (iodide and bromide) to endo- and exo-2-substituted norbornene derivatives have been investigated. The main products of the reactions resulted from the regioselective addition of nucleophiles to the double bond of norbornene derivatives. Products resulting from the Wagner-Meerwein type rearrangement were also isolated in considerable amounts. All of the reactions gave the addition products in reasonably good yields with high regioselectivity. The endo/exo selectivity, on the other hand, changed depending on the nucleophile and the substrate.

Subject Keywords

Remote substituent effects, Endo/exo selectivity, Regioselectivity, Nucleophilic additions, Pi-facial selectivity

URI

https://hdl.handle.net/11511/55438

Journal

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES

Collections

Department of Chemistry, Article

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Citation Formats

A. İŞLEYEN, T. SAYRAÇ, and Ö. Doğan, “Boron trifluoride mediated addition of nucleophiles to endo- and exo-substituted norbornene derivatives,” ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, pp. 109–118, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/55438.