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

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.

SUBMITTER: Wu D

PROVIDER: S-EPMC5952552 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature

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

Wu Di D Ganguly Rakesh R Li Yongxin Y Hoo Sin Ni SN Hirao Hajime H Kinjo Rei R

Chemical science 20150915 12

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 process ...[more]

PMID: 29861951

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