Stereoselectivity ratios in a simple Diels-Alder reaction in aqueous salt solutions of alcohols
| Title | Stereoselectivity ratios in a simple Diels-Alder reaction in aqueous salt solutions of alcohols |
| Publication Type | Journal Article |
| Year of Publication | 2005 |
| Authors | Deshpande, SS, Kumar, A |
| Journal | Tetrahedron |
| Volume | 61 |
| Issue | 33 |
| Pagination | 8025-8030 |
| Date Published | AUG |
| Type of Article | Article |
| ISSN | 0040-4020 |
| Keywords | aqueous alcohols, Diels-Alder reaction, endolexo ratios, salts |
| Abstract | This is the first exhaustive report on the variation of stereoselectivity ratios for a simple Diels-Alder reaction between cyclopentadiene and methyl acrylate. The reaction was carried out in aqueous mixtures of methanol, ethanol, propan-1-ol and butan-1-ol in presence of LiClO4, LiCl, NaCl, KCl, CaCl2 and MgCl2. The endo sterecisomer decreases with the increase in carbon chain length of the alcohol. However, LiClO4, a salting-in agent in water becomes salting-out in aqueous mixtures of alcohols. The solvent properties, thus can be attuned by adjusting the amount of solvents and salts. (c) 2005 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2005.06.010 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.645 |
Divison category:
Physical and Materials Chemistry