Publication details
A DFT Study of Radical Z/E Isomerization of BBr2C2H2Br
| Authors | |
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| Year of publication | 2018 |
| Type | Conference abstract |
| MU Faculty or unit | |
| Citation | |
| 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. |