Stepwise formation of 1,3-diazolium-4-thiolates by münchnone cycloadditions: promising candidates for nonlinear optics
Stepwise formation of 1,3-diazolium-4-thiolates by münchnone cycloadditions: promising candidates for nonlinear optics
An improved preparation of mesoionic heterocycles 1,3-diazolium-4-thiolates by [3 + 2] cycloadditions of münchnones with aryl isothiocyanates is reported. The process takes place with high or complete regioselectivity, and fast and clean transformations are observed under microwave heating in DMF. DFT calculations support that this cycloaddition proceeds preferably through a stepwise mechanism. Given the pattern substitution around the mesoionic ring resulting in a push–pull system, theoretical estimations predict large hyperpolarizabilities in some cases, which is typical of molecules exhibiting nonlinear optical responses.
4201-4205
Cantillo, David
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Ávalos, Martín
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Babiano, Reyes
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Cintas, Pedro
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Jiménez, José L.
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Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
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Porro, Rocío
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2 May 2014
Cantillo, David
87273376-7777-4726-bbf9-505104580fad
Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Porro, Rocío
6decfdc7-309b-46b4-88e1-4ff23e505b95
Cantillo, David, Ávalos, Martín, Babiano, Reyes, Cintas, Pedro, Jiménez, José L., Light, Mark E., Palacios, Juan C. and Porro, Rocío
(2014)
Stepwise formation of 1,3-diazolium-4-thiolates by münchnone cycloadditions: promising candidates for nonlinear optics.
Journal of Organic Chemistry, 79 (9), .
(doi:10.1021/jo500349g).
Abstract
An improved preparation of mesoionic heterocycles 1,3-diazolium-4-thiolates by [3 + 2] cycloadditions of münchnones with aryl isothiocyanates is reported. The process takes place with high or complete regioselectivity, and fast and clean transformations are observed under microwave heating in DMF. DFT calculations support that this cycloaddition proceeds preferably through a stepwise mechanism. Given the pattern substitution around the mesoionic ring resulting in a push–pull system, theoretical estimations predict large hyperpolarizabilities in some cases, which is typical of molecules exhibiting nonlinear optical responses.
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e-pub ahead of print date: 10 April 2014
Published date: 2 May 2014
Identifiers
Local EPrints ID: 385737
URI: http://eprints.soton.ac.uk/id/eprint/385737
ISSN: 0022-3263
PURE UUID: a04cf3d6-783e-4810-981e-279f0a24a3c1
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Date deposited: 21 Jan 2016 14:51
Last modified: 15 Mar 2024 03:01
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Contributors
Author:
David Cantillo
Author:
Martín Ávalos
Author:
Reyes Babiano
Author:
Pedro Cintas
Author:
José L. Jiménez
Author:
Juan C. Palacios
Author:
Rocío Porro
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