Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents

James Sherwood, Mario De bruyn, Andri Constantinou, Laurianne Moity, Con Robert McElroy, Thomas J. Farmer, Tony Duncan, Warwick D. Raverty, Andrew J. Hunt, James H. Clark

Chemical Communications · 2014 · 465 citations · 25 references

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Abstract

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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