Zinc monoglycerolate as a catalyst for the conversion of 1,3- and higher diols to diurethanes

Sanjitha Kulasegaram, Uzma Shaheen, Terence William Turney, Will Peter Gates, Antonio Frank Patti

Research output: Contribution to journalArticleResearchpeer-review

1 Citation (Scopus)

Abstract

A 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.
Original languageEnglish
Pages (from-to)47809-47812
Number of pages4
JournalRSC Advances
Volume5
Issue number59
DOIs
Publication statusPublished - 2015

Cite this