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

Juntian Zhang, Annika C.S. Page, Vignesh Palani, Junhua Chen, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)5550-5553
Number of pages4
JournalOrganic Letters
Volume20
Issue number18
DOIs
StatePublished - Sep 21 2018

Bibliographical note

Funding Information:
Support for this research was provided by the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R01 GM65597, then R35 GM127097). A.C.S.P. and V.P. appreciate the support of a Gleysteen−Heisig fellowship for undergraduate students. Some of the NMR data were obtained with an instrument acquired with funds from the NIH Shared Instrumentation Grant program (S10OD011952).

Funding Information:
Support for this research was provided by the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R01 GM65597, then R35 GM127097). A.C.S.P. and V.P. appreciate the support of a Gleysteen-Heisig fellowship for undergraduate students. Some of the NMR data were obtained with an instrument acquired with funds from the NIH Shared Instrumentation Grant program (S10OD011952).

Publisher Copyright:
Copyright © 2018 American Chemical Society.

Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.

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