Related Experiment Video
Updated: May 29, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Triazole-Au(I) complex as chemoselective catalyst in promoting propargyl ester rearrangements
Dawei Wang1, Yanwei Zhang, Rong Cai
1Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.
Abstract:
Triazole-Au (TA-Au) catalysts were employed in several transformations involving propargyl ester rearrangement. Good chemoselectivity was observed, which allowed the effective activation of the alkyne without affecting the reactivity of the allene ester intermediates. These results led to the investigation of the preparation of allene ester intermediates with TA-Au catalysts under anhydrous conditions. As expected, the desired 3,3-rearrangement products were obtained in excellent yields (generally >90% yields with 1% loading). Besides the typical ester migrating groups, carbonates and carbamates were also found to be suitable for this transformation, which provided a highly efficient, practical method for the preparation of substituted allenes.
More Related Videos
07:56Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane