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

James Sherwood; Mario De bruyn; Andri Constantinou; Laurianne Moity; C. Rob McElroy; Thomas J. Farmer; Tony Duncan; Warwick Raverty; Andrew J. Hunt; James H. Clark

doi:10.1039/C4CC04133J

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

James Sherwood,^a Mario De bruyn,^a Andri Constantinou,^a Laurianne Moity,^a C. Rob McElroy,^a Thomas J. Farmer,^a Tony Duncan,^b Warwick Raverty,^b Andrew J. Hunt^a and James H. Clark*^a

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* Corresponding authors

^a Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, York, UK
E-mail: james.clark@york.ac.uk
Tel: +44 (0)1904 322559

^b Circa Group Pty Ltd, 551 Burwood Highway, Knoxfield, Victoria, Australia
E-mail: tony.duncan@circagroup.com.au
Tel: +61 (3)9955904

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.

Chemical Communications

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

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

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