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Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene
Di Wu1, Rakesh Ganguly2, Yongxin Li2
1Division of Chemistry and Biological Chemistry , School of Physical and Mathematical Sciences , Nanyang Technological University , Singapore 637371 , Singapore . Email: rkinjo@ntu.edu.sg ;
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.
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