Syrgiannis, Z., Koutsianopoulos, F., Muir, K.W. and Elemes, Y. (2009) Reaction of a triazolinedione with simple alkenes: isolation and characterization of hydration products. Tetrahedron Letters, 50(3), pp. 277-280. (doi: 10.1016/j.tetlet.2008.10.150)
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Abstract
The reaction of N-phenyltriazolinedione with three simple alkyl-substituted alkenes in water/alcohol or water/acetone solution was found to give a mixture of the corresponding ene and water addition products. The new hydration products were characterized by spectroscopy, and in one case, also by X-ray diffraction analysis. Thermodynamic parameters were determined for the reactions involving 2-methylbut-2-ene, TriME, and 2,3-dimethylbut-2-ene, TetraMe, in accordance with an ‘SN2-like’, nucleophilic attack on a closed aziridinium imide (AI) intermediate by water.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Muir, Dr Kenneth |
| Authors: | Syrgiannis, Z., Koutsianopoulos, F., Muir, K.W., and Elemes, Y. |
| Subjects: | Q Science > QD Chemistry |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Tetrahedron Letters |
| ISSN: | 0040-4039 |
| ISSN (Online): | 1873-3581 |
| Published Online: | 05 November 2008 |
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