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Stepwise cycloadditions of mesoionic systems: thionation of thioisomunchnones by isothlocyanates

Stepwise cycloadditions of mesoionic systems: thionation of thioisomunchnones by isothlocyanates
Stepwise cycloadditions of mesoionic systems: thionation of thioisomunchnones by isothlocyanates
An unusual thionation strategy of mesoionic compounds with aryl isothiocyanates enables a facile synthesis of 1,3-thiazolium-4-thiolate systems. The mechanistic pathway of such a transformation most likely involves a stepwise 1,3-dipolar cycloaddition, which is supported by theoretical calculations performed with a two-layer hybrid method (B3LYP/6-31G(d):PM3).
hydroxide, chemistry
1523-7060
1079-1082
Cantillo, D.
47ac6c65-67f8-4102-b749-344a6bdf0ba9
Avalos, M.
d6c0ff76-2d77-4fe6-89b5-463404a42de0
Babiano, R.
d79f2a4d-a2e3-4f73-8e58-65eee2a9f88a
Cintas, P.
d4420202-106c-4e8a-b903-5deef99e6a39
Jimenez, J.L.
b07affd8-4345-44a9-b7b0-582c0d76bcf7
Light, M.E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, J.C.
db0e8c94-0385-4349-91a1-b0b2e03f4aab
Cantillo, D.
47ac6c65-67f8-4102-b749-344a6bdf0ba9
Avalos, M.
d6c0ff76-2d77-4fe6-89b5-463404a42de0
Babiano, R.
d79f2a4d-a2e3-4f73-8e58-65eee2a9f88a
Cintas, P.
d4420202-106c-4e8a-b903-5deef99e6a39
Jimenez, J.L.
b07affd8-4345-44a9-b7b0-582c0d76bcf7
Light, M.E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, J.C.
db0e8c94-0385-4349-91a1-b0b2e03f4aab

Cantillo, D., Avalos, M., Babiano, R., Cintas, P., Jimenez, J.L., Light, M.E. and Palacios, J.C. (2008) Stepwise cycloadditions of mesoionic systems: thionation of thioisomunchnones by isothlocyanates. Organic Letters, 10 (6), 1079-1082. (doi:10.1021/ol702929k).

Record type: Article

Abstract

An unusual thionation strategy of mesoionic compounds with aryl isothiocyanates enables a facile synthesis of 1,3-thiazolium-4-thiolate systems. The mechanistic pathway of such a transformation most likely involves a stepwise 1,3-dipolar cycloaddition, which is supported by theoretical calculations performed with a two-layer hybrid method (B3LYP/6-31G(d):PM3).

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Published date: 2008
Keywords: hydroxide, chemistry

Identifiers

Local EPrints ID: 54433
URI: https://eprints.soton.ac.uk/id/eprint/54433
ISSN: 1523-7060
PURE UUID: 8b07385b-79e3-4caf-8ff4-4d52ec2de9a8
ORCID for M.E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 06 Aug 2008
Last modified: 20 Jul 2019 01:10

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Contributors

Author: D. Cantillo
Author: M. Avalos
Author: R. Babiano
Author: P. Cintas
Author: J.L. Jimenez
Author: M.E. Light ORCID iD
Author: J.C. Palacios

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