Observation of Spontaneous C=C Bond Breaking in the Reaction between Atomic Boron and Ethylene in Solid Neon

Jiwen Jian; Hailu Lin; Mingbiao Luo; Mohua Chen; Mingfei Zhou

doi:10.1002/anie.201603345

Observation of Spontaneous C=C Bond Breaking in the Reaction between Atomic Boron and Ethylene in Solid Neon

Angew Chem Int Ed Engl. 2016 Jul 11;55(29):8371-4. doi: 10.1002/anie.201603345. Epub 2016 May 30.

Authors

Jiwen Jian¹, Hailu Lin^{1

2}, Mingbiao Luo², Mohua Chen¹, Mingfei Zhou³

Affiliations

¹ Collaborative Innovation Center of Chemistry for Energy Materials, Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Fudan University, Shanghai, 200433, China.
² Department of Applied Chemistry, East China Institute of Technology, Nanchang, Jiangxi Province, 330013, China.
³ Collaborative Innovation Center of Chemistry for Energy Materials, Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Fudan University, Shanghai, 200433, China. mfzhou@fudan.edu.cn.

PMID: 27240114
DOI: 10.1002/anie.201603345

Abstract

A ground-state boron atom inserts into the C=C bond of ethylene to spontaneously form the allene-like compound H2 CBCH2 on annealing in solid neon. This compound can further isomerize to the propyne-like HCBCH3 isomer under UV light excitation. The observation of this unique spontaneous C=C bond insertion reaction is consistent with theoretical predictions that the reaction is thermodynamically exothermic and kinetically facile. This work demonstrates that the stronger C=C bond, rather than the less inert C-H bond, can be broken to form organoboron species from the reaction of a boron atom with ethylene even at cryogenic temperatures.

Keywords: C=C bond activation; IR spectroscopy; boron; ethylene; matrix isolation.

Publication types

Research Support, Non-U.S. Gov't