Related Experiment Video
Updated: Apr 2, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Diversity-oriented heterocyclic synthesis using divergent reactivity of N-substituted iso(thio)cyanates
Jean-François Vincent-Rocan1, Joshua S Derasp1, André M Beauchemin1
1Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada. andre.beauchemin@uottawa.ca.
Abstract:
Carbon-substituted isocyanates and isothiocyanates are common building blocks in organic synthesis. In contrast, synthetic uses of N-substituted isocyanates and isothiocyanates are severely underdeveloped: few have been reported and their reactivity had not been compared. Herein, we compare the reactivity of blocked (masked) N-isocyanate and N-isothiocyanate precursors in cascade reactions. Divergent reactivity is observed with secondary propargylic and allylic systems, leading to new syntheses of imidazolones, thiazolidines, and a tool to form complex azomethine imines.
Related Concept Videos
Cycloaddition Reactions: Overview
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)