Elucidating the Trends in Reactivity of Aza‐1,3‐Dipolar Cycloadditions
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DOI: 10.1002/ejoc.201800572
Abstract: This report describes a density functional theory investigation into the reactivities of a series of aza-1,3-dipoles with ethylene at the BP86/TZ2P level. A benchmark study was carried out using QMflows, a newly developed program for… read more here.
Keywords: dipolar cycloadditions; elucidating trends; trends reactivity; reactivity ... See more keywords
Enantioselective 1,3-Dipolar (5+3) Cycloadditions of Oxidopyrylium Ylides and Vinylcyclopropanes toward 9-Oxabicyclononanes.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01037
Abstract: We have developed an efficient and mild enantioselective palladium-catalyzed (5+3) cycloaddition of vinylcyclopropanes and oxidopyrylium ylides generated in situ from benzopyranones, in the presence of a chiral PHOX ligand. These reactions afford various highly functionalized… read more here.
Keywords: oxidopyrylium ylides; cycloadditions oxidopyrylium; enantioselective dipolar; vinylcyclopropanes toward ... See more keywords
Regio- and Diastereoselective 1,3-Dipolar Cycloadditions of 1,2,4-Triazin-1-ium Ylides: a Straightforward Synthetic Route to Polysubstituted Pyrrolo[2,1-f][1,2,4]triazines
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DOI: 10.1021/acsomega.2c02276
Abstract: A synthetic strategy to pyrrolo[2,1-f][1,2,4]triazines is reported. We show that various synthetically easily accessible 1,2,4-triazines can be efficiently alkylated under mild conditions to provide the corresponding 1-alkyl-1,2,4-triazinium salts. These bench-stable salts serve as precursors to… read more here.
Keywords: regio diastereoselective; triazin ium; diastereoselective dipolar; cycloadditions triazin ... See more keywords
Nucleophilicity and Electrophilicity Parameters for Predicting Absolute Rate Constants of Highly Asynchronous 1,3-Dipolar Cycloadditions of Aryldiazomethanes.
Sign Up to like & getrecommendations! Published in 2018 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.8b09995
Abstract: Kinetics of the reactions of aryldiazomethanes (ArCHN2) with benzhydrylium ions (Ar2CH+) have been measured photometrically in dichloromethane. The resulting second-order rate constants correlate linearly with the electrophilicities E of the benzhydrylium ions which allowed us… read more here.
Keywords: dipolar cycloadditions; bond; rate constants; rate ... See more keywords
Mechanistic DFT Study of 1,3-Dipolar Cycloadditions of Azides with Guanidine
Sign Up to like & getrecommendations! Published in 2023 at "Molecules"
DOI: 10.3390/molecules28052342
Abstract: Density functional calculations SMD(chloroform)//B3LYP/6-311+G(2d,p) were employed in the computational study of 1,3-dipolar cycloadditions of azides with guanidine. The formation of two regioisomeric tetrazoles and their rearrangement to cyclic aziridines and open-chain guanidine products were modeled.… read more here.
Keywords: azides guanidine; cycloadditions azides; study dipolar; nitrogen ... See more keywords