Wednesday, October 24, 2012

The hexadehydro-Diels-Alder reaction

Thomas R. Hoye, Beeraiah Baire, Dawen Niu, Patrick H. Willoughby & Brian P. Woods

 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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