Stereoselectivity ratios in a simple Diels-Alder reaction in aqueous salt solutions of alcohols |
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Authors: | Suvarna S. Deshpande |
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Affiliation: | Physical Chemistry Division, National Chemical Laboratory, Pune 411 008, Maharashtra, India |
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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 stereoisomer 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. |
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Keywords: | Diels-Alder reaction Endo/exo ratios Aqueous alcohols Salts |
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