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