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Azodicarboxamides vs. azodicarboxylates in reactions against thioisomünchnones: 1,3-dipolar cycloaddition or nucleophilic addition?

Azodicarboxamides vs. azodicarboxylates in reactions against thioisomünchnones: 1,3-dipolar cycloaddition or nucleophilic addition?
Azodicarboxamides vs. azodicarboxylates in reactions against thioisomünchnones: 1,3-dipolar cycloaddition or nucleophilic addition?
This communication presents the first study on the use of azodicarboxamides against mesoionic heterocycles as 1,3-dipoles. The reactions yield thioureido compounds. Their formation could be explained, on the basis of experimental results and preliminary theoretical calculations, by a nucleophilic addition followed by rearrangement; however, a formal 1,3-dipolar cycloaddition and subsequent fragmentation and rearrangement of the transient cycloadducts could not be ruled out. Reactions are carried out in refluxing toluene and are complete in 90–240 min. Structural elucidation of the products is based on single-crystal X-ray analysis, as well as other spectroscopic data and 2D-NMR correlations
1434-193X
1648-1652
Sánchez, Bárbara
602798bd-b89e-49dc-9e76-f0a0cd28144f
López, Ignacio
215a6254-7805-40e9-a90d-878a966e6dbb
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Silvero, Guadalupe
8e6975cc-88ec-4809-8040-bc84413d57d6
Bravo, José Luis
068aecea-88b9-4b0f-8448-3180c7e4c30c
Sánchez, Bárbara
602798bd-b89e-49dc-9e76-f0a0cd28144f
López, Ignacio
215a6254-7805-40e9-a90d-878a966e6dbb
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Silvero, Guadalupe
8e6975cc-88ec-4809-8040-bc84413d57d6
Bravo, José Luis
068aecea-88b9-4b0f-8448-3180c7e4c30c

Sánchez, Bárbara, López, Ignacio, Light, Mark E., Silvero, Guadalupe and Bravo, José Luis (2010) Azodicarboxamides vs. azodicarboxylates in reactions against thioisomünchnones: 1,3-dipolar cycloaddition or nucleophilic addition? European Journal of Organic Chemistry, 2010 (9), 1648-1652. (doi:10.1002/ejoc.200901349).

Record type: Article

Abstract

This communication presents the first study on the use of azodicarboxamides against mesoionic heterocycles as 1,3-dipoles. The reactions yield thioureido compounds. Their formation could be explained, on the basis of experimental results and preliminary theoretical calculations, by a nucleophilic addition followed by rearrangement; however, a formal 1,3-dipolar cycloaddition and subsequent fragmentation and rearrangement of the transient cycloadducts could not be ruled out. Reactions are carried out in refluxing toluene and are complete in 90–240 min. Structural elucidation of the products is based on single-crystal X-ray analysis, as well as other spectroscopic data and 2D-NMR correlations

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Published date: March 2010

Identifiers

Local EPrints ID: 179391
URI: http://eprints.soton.ac.uk/id/eprint/179391
ISSN: 1434-193X
PURE UUID: d1de24ef-2648-4c92-9332-69760f88d221
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 01 Apr 2011 08:41
Last modified: 07 Oct 2020 07:23

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