A DFT Study of Radical Z/E Isomerization of BBr2C2H2Br

SEMRÁD, Hugo and Markéta MUNZAROVÁ. A DFT Study of Radical Z/E Isomerization of BBr2C2H2Br. In 16th Central European Symposium on Theoretical Chemistry. 2018.

Basic information

• Original name: A DFT Study of Radical Z/E Isomerization of BBr2C2H2Br
• Name in Czech: DFT studie radikálové izomerizace BBr2C2H2Br
• Authors: SEMRÁD, Hugo and Markéta MUNZAROVÁ.
• Edition: 16th Central European Symposium on Theoretical Chemistry, 2018.

Other information

• Original language: English
• Type of outcome: Conference abstract
• Field of Study: 10403 Physical chemistry
• Country of publisher: Czech Republic
• Confidentiality degree: is not subject to a state or trade secret
• Organization unit: Faculty of Science

Abstract

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.