Synthesis of dihydrothiophenes by an amino-directed thioisomünchnone-alkene cycloaddition reaction
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)
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Official URL: http://dx.doi.org/10.1002/1099-0690(200106)2001:11...
Description/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.
| Item Type: | Article |
|---|---|
| Uncontrolled 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 |
| Related URLs: | http://dx.doi.org/10.1002/1099...3.0.CO;2-L |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| ePrint ID: | 19380 |
| URI: | http://eprints.soton.ac.uk/id/eprint/19380 |
| Deposited On: | 13 Feb 2006 |
| Last Modified: | 02 Mar 2012 13:26 |
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