Purification‐Free, Small‐Scale Synthesis of Isothiocyanates by Reagentless Fragmentation of Polymer‐Supported 1, 4, 2‐Oxathiazoles. Issue 5 (5th December 2013)

• Record Type: Journal Article
• Authors: Burkett, Brendan A.; Fu, Pincheng; Hewitt, Russell J.; Ng, Su Ling; Toh, Joel D. W.
• Is Part Of: European journal of organic chemistry. Issue 5(2014)
• Page Start: 1053
• Page End: 1058
• Publication Date: 2013-12-05
• Subjects: Solid‐phase synthesis -- Cycloaddition -- Immobilization -- Polymers -- Sulf­ur -- Isothiocyanates; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301535
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The synthesis of isothiocyanates (ITCs) by employing polymer‐supported 1, 4, 2‐oxathiazoles is described. The ITCs are obtained in moderate yields and high purity through a reagentless, thermal fragmentation of polymer‐supported 1, 4, 2‐oxathiazoles that are obtained by trapping nitrile oxides with polymer‐supported thiocarbonates. Abstract : A purification‐free, small‐scale synthesis for isothiocyanates (ITCs) is reported that proceeds through a catch‐and‐release system. This is a convenient method to produce small quantities of ITCs in high purity for screening purposes.