Journal
CHEMICAL SCIENCE
Volume 6, Issue 12, Pages 7150-7155Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc03174e
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- Nanyang Technological University (NTU)
- PSF/A*STAR (SERC) of Singapore [1321202066]
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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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