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Stereoselectivity of acetalization and ketalization reactions of giycerol and its modified derivatives

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3 Author(s)
Keyan, Wang ; Department of Chemistry, Tsinghua University, Beijing 100084 ; Zengjia, Yang ; Qinzhu, Wang

Twenty-one 1, 3-dioxdanes with varieties of substituents at 2, 4 positions were synthesized by acid-catalyzed acetalization and ketalization reactions of glycerol and its modified derivatives. The assignment and quantitative analyses of thermodynamically equilibrated cis- and trans-1, 3-dioxolanes were completed by 1H-NMR. The stereoselective regularity was found in acetalization and ketalization reactions of glycerol and its modified derivatives. The stereoselective regularity of the condensation reactions was reasonablyexplained by anomeric effect and 2, 4-nonbonded interaction.

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Tsinghua Science and Technology  (Volume:2 ,  Issue: 4 )