Trapping Reactive Intermediates by Mechanochemistry: Elusive Aryl N-Thiocarbamoylbenzotriazoles as Bench-Stable Reagents

DOI: 10.1002/anie.201502026
PMID: 26068712

Authors: Vjekoslav Štrukil (McGill University) , Davor Gracin (Ruđer Bošković Institute) , Oxana Magdysyuk (Diamond Light Source) , Robert Dinnebier (Max Planck Institute for Solid State Research, Stuttgart) , Tomislav Friscic (McGill University)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Angewandte Chemie International Edition , VOL 54 (29) , PAGES 8440 - 8443

State: Published (Approved)
Published: July 2015

Abstract: Monitoring of mechanochemical thiocarbamoylation by in situ Raman spectroscopy revealed the formation of aryl N-thiocarbamoylbenzotriazoles, reactive intermediates deemed unisolable in solution. The first-time isolation and structural characterization of these elusive molecules demonstrates the ability of mechanochemistry to access otherwise unobtainable intermediates and offers a new range of masked isothiocyanate reagents.

Journal Keywords: Mechanochemistry; reactive intermediates; thiocarbamoylation; thiourea

Subject Areas: Chemistry

Facility: Canadian Light Source