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Updated: Aug 31, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
A predictive journey towards trans-thioamides/amides
Michele Tomasini1,2, Jin Zhang3, Hui Zhao3
1Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, C/Maria Aurèlia Capmany 69, 17003, Girona, Catalonia, Spain. albert.poater@udg.edu.
Abstract:
The cis-trans isomerization of (thio)amides was studied by DFT calculations to get the model for the higher preference for the cis conformation by guided predictive chemistry, suggesting how to select the alkyl/aryl substituents on the C/N atoms that lead to the trans isomer. Multilinear analysis, together with cross-validation analysis, helped to select the best fitting parameters to achieve the energy barriers of the cis to trans interconversion, as well as the relative stability between both isomers. Double experimental check led to the synthesis of the best trans candidate with sterically demanding t-butyl substituents, confirming the utility of predictive chemistry, bridging organic and computational chemistry.
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