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Title: Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene
Authors: Wu, Di
Ganguly, Rakesh
Li, Yongxin
Hoo, Sin Ni
Hirao, Hajime
Kinjo, Rei
Keywords: Cycloaddition
Reaction Pathways
Issue Date: 2015
Source: Wu, D., Ganguly, R., Li, Y., Hoo, S. N., Hirao, H., & Kinjo, R. (2015). Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene. Chemical Science, 6(12), 7150-7155. doi:10.1039/c5sc03174e
Series/Report no.: Chemical Science
Abstract: Under ambient conditions, a [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine 1 with ethylene afforded a bicyclo[2.2.2] derivative 2, which was structurally characterized. The cyclization process was found to be reversible, and thus retro-[4 + 2] cycloaddition reproduced 1 quantitatively, concomitant with the release of ethylene. Compound 1 reacted regio-selectively and stereo-selectively with styrene derivatives and norbornene, respectively, and these processes were found to be reversible too. Computational studies determined the reaction pathways which were consistent with the regio-selectivity observed in the reaction of styrene, and the reaction was suggested to be essentially concerted but highly asynchronous.
ISSN: 2041-6520
DOI: 10.1039/C5SC03174E
Rights: © 2015 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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