Atypical Mode of [3 + 2]-Cycloaddition: Pseudo-1,3-dipole Behavior in Reactions of Electron-Deficient Thioamides with Benzynes

Organic Letters
Juntian ZhangThomas R Hoye

Abstract

Thioamides bearing electron-withdrawing groups on the thiocarbonyl carbon atom react with benzynes [generated by the hexadehydro-Diels-Alder cycloisomerization] in an unprecedented fashion. Namely, the dihydrobenzothiazole products are consistent with a pathway involving initial formation of a stabilized ammonium ylide by a rare type of [3 + 2]-cycloaddition reaction. The fate of this species depends upon the nature of the R group(s) attached to the ylide nitrogen atom. The demonstration of new modes of reactivity represents the major advance arising from this study.

References

Jan 12, 2010·Journal of the American Chemical Society·Paul H-Y CheongK N Houk
Mar 8, 2011·Chemical Communications : Chem Comm·Jonathan ClaydenDaniel J Tetlow
Oct 11, 2014·Journal of the American Chemical Society·Jose M MedinaK N Houk
Aug 14, 2015·The Journal of Organic Chemistry·Daniel J MarellKeith T Kuwata

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