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Synthesis of dihydrothiophenes by an amino-directed thioisomünchnone-alkene cycloaddition reaction

Synthesis of dihydrothiophenes by an amino-directed thioisomünchnone-alkene cycloaddition reaction
Synthesis of dihydrothiophenes by an amino-directed thioisomünchnone-alkene cycloaddition reaction
Dihydrothiophenes can easily be obtained by a general protocol involving the reaction of 2-aminothioisomunchnones with electron-deficient alkenes. The overall process can be interpreted as a sequential [3+2] cycloaddition/ring-opening cyclization reaction. The structures of the products could be unequivocally assigned by X-ray diffraction analysis. A theoretical study at a semiempirical level (PM3) with a further single-point refinement of energies at the B3LYP/6-31G(*) level also offers mechanistic insights into the stereochemical outcome.
dihydrothiophenes, dipolar cycloadditions, mesoionic heterocycles, theoretical calculations, anhydro-4-hydroxythiazolium hydroxide system, mesoionic compounds, diastereoselective synthesis, mesomeric betaines, chemistry, dipolarophiles, isomünchnone, derivatives, cyclization, diazoimides
1434-193X
2135-2144
Areces, Pilar
3a8ae816-4a9d-404b-a7a0-d5e69617d474
Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
González, Luis
a5713e63-c42b-4884-af8f-40bc44220e12
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
López, Ignacio
215a6254-7805-40e9-a90d-878a966e6dbb
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Silvero, Guadalupe
8e6975cc-88ec-4809-8040-bc84413d57d6
Areces, Pilar
3a8ae816-4a9d-404b-a7a0-d5e69617d474
Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
González, Luis
a5713e63-c42b-4884-af8f-40bc44220e12
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
López, Ignacio
215a6254-7805-40e9-a90d-878a966e6dbb
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Silvero, Guadalupe
8e6975cc-88ec-4809-8040-bc84413d57d6

Areces, Pilar, Ávalos, Martín, Babiano, Reyes, Cintas, Pedro, González, Luis, Hursthouse, Michael B., Jiménez, José L., Light, Mark E., López, Ignacio, Palacios, Juan C. and Silvero, Guadalupe (2001) Synthesis of dihydrothiophenes by an amino-directed thioisomünchnone-alkene cycloaddition reaction. European Journal of Organic Chemistry, (11), 2135-2144. (doi:10.1002/1099-0690(200106)2001:11<2135::AID-EJOC2135>3.0.CO;2-L).

Record type: Article

Abstract

Dihydrothiophenes can easily be obtained by a general protocol involving the reaction of 2-aminothioisomunchnones with electron-deficient alkenes. The overall process can be interpreted as a sequential [3+2] cycloaddition/ring-opening cyclization reaction. The structures of the products could be unequivocally assigned by X-ray diffraction analysis. A theoretical study at a semiempirical level (PM3) with a further single-point refinement of energies at the B3LYP/6-31G(*) level also offers mechanistic insights into the stereochemical outcome.

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More information

Published date: 2001
Keywords: dihydrothiophenes, dipolar cycloadditions, mesoionic heterocycles, theoretical calculations, anhydro-4-hydroxythiazolium hydroxide system, mesoionic compounds, diastereoselective synthesis, mesomeric betaines, chemistry, dipolarophiles, isomünchnone, derivatives, cyclization, diazoimides

Identifiers

Local EPrints ID: 19380
URI: https://eprints.soton.ac.uk/id/eprint/19380
ISSN: 1434-193X
PURE UUID: 3e9301a1-5bc5-4d3a-909c-8fb88d8b0fff

Catalogue record

Date deposited: 13 Feb 2006
Last modified: 05 Oct 2018 12:04

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Contributors

Author: Pilar Areces
Author: Martín Ávalos
Author: Reyes Babiano
Author: Pedro Cintas
Author: Luis González
Author: José L. Jiménez
Author: Mark E. Light
Author: Ignacio López
Author: Juan C. Palacios
Author: Guadalupe Silvero

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