Chemical Communications · 2014 · 465 citations · 25 references
Natural SciencesBiochemistryChemistryOrganic ChemistryCellulose BiochemistryCellulose ChemistryBio-derived Solvent SynthesisPolar Aprotic Solvents
Dihydrolevoglucosenone (Cyrene) is a bio-based molecule, derived in two simple steps from cellulose, which demonstrates significant promise as a dipolar aprotic solvent. The dipolarity of dihydrolevoglucosenone is similar to NMP, DMF and sulpholane. Dihydrolevoglucosenone demonstrates similar performance to NMP in a fluorination reaction and the Menschutkin reaction.
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Mortimer J. Kamlet, J.‐L. M. Abboud, Michael H. Abraham et al. · The Journal of Organic Chemistry · 1983 · 3.6K citations