The rapid generation of isothiocyanates in flow

Baumann, Marcus; Baxendale, Ian R.

Abstract

Isothiocyanates are versatile starting materials for a wide range of chemical reactions. However, their high nucleophilic susceptibility means they are best prepared and used immediately. We report here on a flow platform for the fast and efficient formation of isothiocyanates by the direct conversion of easily prepared chloroximes. To expedite this chemistry a flow insert cartridge containing two immobilised reagents is used to affect the chemical transformation which typically eliminates the requirements for any conventional work-up or purification of the reaction stream.

Citation

Baumann, M., & Baxendale, I. R. (2013). The rapid generation of isothiocyanates in flow. Beilstein Journal of Organic Chemistry, 9, 1613-1619. https://doi.org/10.3762/bjoc.9.184

• Journal Article Type: Article
• Acceptance Date: Jul 23, 2013
• Publication Date: Aug 8, 2013
• Deposit Date: Jul 14, 2014
• Publicly Available Date: Jun 1, 2015
• Journal: Beilstein Journal of Organic Chemistry
• Print ISSN: 1860-5397
• Electronic ISSN: 1860-5397
• Publisher: Beilstein-Institut
• Peer Reviewed: Peer Reviewed
• Volume: 9
• Pages: 1613-1619
• DOI: https://doi.org/10.3762/bjoc.9.184
• Keywords: Chloroxime, Dipolar cycloaddition, Flow chemistry, Flow synthesis, Immobilised reagents, Isothiocyanate, Nitrile oxide.
• Public URL: https://durham-repository.worktribe.com/output/1423810