The Journal of Organic Chemistry

Free-radical and anion intermediates in the reactions of 5-halo-2-norbornenes and 3-halonortricyclenes with (trimethyltin) sodium

MS Alnajjar, HG Kuivila

Index: Alnajjar, Mikhail S.; Kuivila, Henry G. Journal of Organic Chemistry, 1981 , vol. 46, # 6 p. 1053 - 1057

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Citation Number: 15

Abstract

The reaction of (trimethy1tin) sodium with exo-5chlore and 5-bromo-2-norbomenea, endo- 5bromo-2-norbomene, and 3-bromo-and 3-iodonortricyclene in tetrahydrofuran has been examined. Use of dicyclohexylphosphine as a trap for intermediate radicals by hydrogen atom transfer showed that the bromides and chloride reacted predominantly by way of free- radical intermediates and by geminate reactions. The geminate products showed ...

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