Observation of Spontaneous C=C Bond Breaking in the Reaction between Atomic Boron and Ethylene in Solid Neon. Issue 29 (30th May 2016)

• Record Type: Journal Article
• Authors: Jian, Jiwen; Lin, Hailu; Luo, Mingbiao; Chen, Mohua; Zhou, Mingfei
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 29(2016)
• Page Start: 8371
• Page End: 8374
• Publication Date: 2016-05-30
• Subjects: boron -- C=C bond activation -- ethylene -- IR spectroscopy -- matrix isolation; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201603345
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : C=C bond activation : A ground‐state boron atom selectively inserts into the strong C=C bond of ethylene in solid neon to spontaneously form the compound H2 CBCH2 . This compound can further isomerize to the less stable isomer HCBCH3 under UV light excitation. Atom colors: B=pink; C=gray; H=white.