Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene

Under ambient conditions, a [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene afforded a bicyclo[2.2.2] derivative , which was structurally characterized. The cyclization process was found to be reversible, and thus retro-[4 + 2] cycloaddition reproduced quantitatively, concomi...

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Published inChemical science (Cambridge) Vol. 6; no. 12; pp. 7150 - 7155
Main Authors Wu, Di, Ganguly, Rakesh, Li, Yongxin, Hoo, Sin Ni, Hirao, Hajime, Kinjo, Rei
Format Journal Article
LanguageEnglish
Published England 01.01.2015
Subjects
Computation
Cycloaddition
Derivatives
Ethylene
Pathways
Styrenes
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Summary:Under ambient conditions, a [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene afforded a bicyclo[2.2.2] derivative , which was structurally characterized. The cyclization process was found to be reversible, and thus retro-[4 + 2] cycloaddition reproduced quantitatively, concomitant with the release of ethylene. Compound 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.
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ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc03174e