Publication details

A DFT Study of Radical Z/E Isomerization of BBr2C2H2Br



Year of publication 2018
Type Conference abstract
MU Faculty or unit

Faculty of Science

Description Haloboration reactions of alkynes represent key elements in many organic synthetic routes, as evidenced in a series of 21 papers by A. Suzuki through 1983-1992.1 During an acetylene bromoboration reaction, (Z)–alkene is formed by the direct addition of boron tribromide to acetylene which undregoes a subsequent isomerization into (E)-dibromo(2-bromovinyl)borane cf. Wang and Uchyiama have proposed a polar isomerization mechanism catalyzed by another BBr3 molecule with a barrier of ca. 26 kcal/mol.2 This is in contrast with recent experimental findings obtained in our department.3 The present DFT study concentrates on an alternative mechanism initiated by a reaction of Z-alkene with the radical Br., whose presence is expected due to the interaction with residual air humidity.

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