Related Experiment Video
Updated: May 27, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Photosensitized Imino-Thiocyanation of Alkenes
Cong Huang1, Zhen-Zhen Xie1, Jie Gao1
1College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
Abstract:
A metal-free photosensitized 1,2-imino-thiocyanation of olefins has been established by using the easily accessible bifunctional reagent S-cyano-N-(diphenylmethylene) thiohydroxylamine. A wide range of olefins were successfully transformed into the corresponding β-iminothiocyanates in moderate to high yields. This protocol stands out for its metal-free nature, broad substrate compatibility, and high atom and step economy, providing an effective strategy for assembling β-amino thiocyanate-containing scaffolds.
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)