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A team of researchers in Professor Thomas Hoye's laboratories, composed
of Dawen Niu, Pat Willoughby, Brian Woods and Beeru Baire, has uncovered
a new type of transformation. They reported last week in Nature (doi:10.1038/nature12492) that reactive benzyne derivatives, formed by the
hexadehydro-Diels-Alder (HDDA) reaction (doi:10.1038/nature11518),
will abstract two hydrogen atoms from a saturated alkane to produce the
corresponding alkene (via oxidation) and benzenoid (via reduction)
disproportionation products. Mechanistic and computational studies all
point to the involvement of a concerted dihydrogen transfer event via a
planar transition structure geometry. The investigators comment, "We are
not aware of any single-step, bimolecular reaction in which two
hydrogen atoms are simultaneously transferred from a saturated alkane."1
1.
"Alkane desaturation by concerted double hydrogen atom transfer to
benzyne," Niu, D.; Willoughby, P. H.; Baire, B.; Woods, B. P.; Hoye, T.
R. Nature 2013, 501, 531-534. (doi:10.1038/nature12492)