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Zinc monoglycerolate as a catalyst for the conversion of 1,3- and higher diols to diurethanes
journal contribution
posted on 2015-01-01, 00:00 authored by S Kulasegaram, U Shaheen, T W Turney, Will GatesWill Gates, A F PattiA green methodology exploring the scope of diurethane synthesis from diols and urea in the presence of a homogeneous catalyst is described. Past reactions of diurethanes have relied heavily on environmentally corrosive reagents such as phosgene. Prior to this work, we have utilized metal glycerolates as homogeneous catalysts in the glycerolysis of urea. Here we explore the synthetic scope of this system with a variety of diols. The conversion to diurethanes is proposed to proceed via an intermediate zinc bound isocyanate ligand, which rearranges to form the terminal urethane in the case of 1,3- and higher diols in good selectivity and yields. With butane 1,2,4-triol the selectivity is exclusively for the 5-membered carbonate, suggesting that the proximity of the second hydroxyl group is critical in forming the ring.
History
Journal
RSC advancesVolume
5Issue
59Pagination
47809 - 47812Publisher
Royal Society of ChemistryLocation
Cambridge, Eng.Publisher DOI
eISSN
2046-2069Language
engPublication classification
C Journal article; C1.1 Refereed article in a scholarly journalCopyright notice
2015, Royal Society of ChemistryUsage metrics
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