Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethyleneElectronic supplementary information (ESI) available: Experimental and calculation details, and crystallographic information for 2, 4a, 4b, 4d, and 6. CCDC 1418724-1418728. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc03174e

Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethyleneElectronic supplementary information (ESI) available: Experimental and calculation details, and crystallographic information for 2, 4a, 4b, 4d, and 6. CCDC 1418724-1418728. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc03174e

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, c...

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Hauptverfasser: Wu, Di, Ganguly, Rakesh, Li, Yongxin, Hoo, Sin Ni, Hirao, Hajime, Kinjo, Rei
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Kinjo, Rei
description 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. 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.
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title Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethyleneElectronic supplementary information (ESI) available: Experimental and calculation details, and crystallographic information for 2, 4a, 4b, 4d, and 6. CCDC 1418724-1418728. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc03174e
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