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Observation of Spontaneous C=C Bond Breaking in the Reaction between Atomic Boron and Ethylene in Solid Neon
Author(s) -
Jian Jiwen,
Lin Hailu,
Luo Mingbiao,
Chen Mohua,
Zhou Mingfei
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201603345
Subject(s) - ethylene , exothermic reaction , boron , allene , chemistry , photochemistry , propyne , neon , polymer chemistry , organic chemistry , catalysis , argon
A ground‐state boron atom inserts into the C=C bond of ethylene to spontaneously form the allene‐like compound H 2 CBCH 2 on annealing in solid neon. This compound can further isomerize to the propyne‐like HCBCH 3 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.