Thomas R. Hoye, Beeraiah Baire, Dawen Niu, Patrick H. Willoughby & Brian P. Woods
http://www.nature.com/nature/journal/v490/n7419/full/nature11518.html
The authors report a the hexadehydro-diels-alder (HDDA) reaction as a
way to generate reactive aryne species, which can be trapped resulting
in interesting benzenoid compounds. Originally the group had tried to
prepare a ketotetrayne from molecule 13, but ended up with molecule 15
and proposed the mechanism shown below. They tested molecule 21 in an
HDDA reaction to produce molecule 22 in good yield. They also tested
intramolecular HDDA reactions with different hexatriene molecules to get
various benzenoids.
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