The Journal of Organic Chemistry

Electrophilic bromination of aromatic conjugated olefins. II. Mechanism of the dual-path additions in stilbene bromination. Evidence from multiple substituent effects for …

JE Dubois, MF Ruasse

Index: Dubois,J.-E.; Ruasse,M.-F. Journal of Organic Chemistry, 1973 , vol. 38, # 3 p. 493 - 499

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Citation Number: 20

Abstract

Kinetic data for the bromination of disubstituted stilbenes, XCeH, C, H= C, HCsHdY, in methanol are interpreted in terms of the dual-path addition mechanism in which two pathways (with rate constants k, and k,, respectively), leading to discrete carbonium ions, C,+ and Cyf, are involved. The nonlinear free energy relationship corresponding to this scheme is log (k/ko)= log [(kz+ kv)/&]= log [lOpa" x'+" Buy+ 10pa" y'+ pP" x], where pa and ...