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Synthetic Strategies to Access Fluorinated Azoles. [PDF]
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Amide Synthesis by Nucleophilic Attack of Vinyl Azides
Angewandte Chemie - International Edition, 2014AbstractA method for the synthesis of amide‐containing molecules was developed using vinyl azides as an enamine‐type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3⋅OEt2.
Feng-Lian Zhang, Yi-Feng Wang, Xu Zhu
exaly +4 more sources
Angewandte Chemie International Edition in English, 1975
AbstractThis review is designed to demonstrate the versatility of vinyl azides in organic reactions. The reactive azide function is susceptible to thermolysis, photolysis, cycloadditions, and attack by nucleophiles and electrophiles. The neighboring double bond accentuates the reactivity of the azide function and provides additional intramolecular ...
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AbstractThis review is designed to demonstrate the versatility of vinyl azides in organic reactions. The reactive azide function is susceptible to thermolysis, photolysis, cycloadditions, and attack by nucleophiles and electrophiles. The neighboring double bond accentuates the reactivity of the azide function and provides additional intramolecular ...
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New Methods for the Synthesis of Vinyl Azides
Angewandte Chemie International Edition in English, 1971AbstractA critical survey of synthetic approaches to vinyl azides is presented, focusing especially on stereo‐ and regiochemical problems. The com bined procedure of azidohalogenation of olefins followed by dehydrohalogenation, leads to regiospecific and, in the case of ionic additions, also to stereospecific formation of vinyl azides.
Gerrit L'abbé, Alfred Hassner
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Indium(III) Catalyzed Reactions of Vinyl Azides and Indoles
Organic Letters, 2020Indium trichloride catalyzes the reaction of vinyl azides with unfunctionalized indoles to give vinyl indoles. This is the first example of displacement of the azide group by a carbon nucleophile while preserving the vinyl function. The protocol employs very mild reaction conditions and offers excellent yields of diverse 3-vinyl indoles. It is amenable
Atul A More, Alex M Szpilman
exaly +3 more sources
The Journal of Organic Chemistry, 2014
Photolysis of vinylazide 1, which has a built-in acetophenone triplet sensitizer, in argon-saturated toluene results in azirine 2, whereas irradiation in oxygen-saturated toluene yields cyanide derivatives 3 and 4. Laser flash photolysis of azide 1 in argon-saturated acetonitrile shows formation of vinylnitrene 1c, which has a λmax at ∼300 nm and a ...
Sridhar, Rajam +11 more
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Photolysis of vinylazide 1, which has a built-in acetophenone triplet sensitizer, in argon-saturated toluene results in azirine 2, whereas irradiation in oxygen-saturated toluene yields cyanide derivatives 3 and 4. Laser flash photolysis of azide 1 in argon-saturated acetonitrile shows formation of vinylnitrene 1c, which has a λmax at ∼300 nm and a ...
Sridhar, Rajam +11 more
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Electron‐Catalyzed Fluoroalkylation of Vinyl Azides
Chemistry – A European Journal, 2016AbstractThe transition‐metal free fluoroalkylation of vinyl azides is herein reported. This operationally simple reaction employs the Togni reagent as a CF3 source, Bu4NI as an initiator, and occurs under electron catalysis. A range of readily prepared starting materials are functionalized using this approach to produce both phenanthridines and ...
Emily G. Mackay, Armido Studer
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Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides
European Journal of Organic Chemistry, 2020Reported is the construction, and facile base‐mediated conversation of ten differently substituted 3‐azido E‐vinyl sulfones (γ‐azido‐α,β‐unsaturated sulfones) into their isomeric vinyl azide counterparts. The requisite 3‐azido E‐vinyl sulfones were prepared from 3‐bromo E‐vinyl sulfones, which in turn were accessed from allyl sulfones via a bromination‐
Collins, Niall +3 more
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Canadian Journal of Chemistry, 1973
Reaction of vinyl azides with nitrosyl tetrafluoroborate yields 1,2,5-oxadiazoles and 1,2,4-oxadiazoles depending on the structure of the azide. Reaction of 1,2-dialkyl vinyl azides with nitryl tetrafluoroborate gives 2-oxo-1,2,5-oxadiazoles in high yields whereas 1-aryl-2-alkyl vinyl azides gave moderate yields of 3-aryl-1,2,5-oxadiazoles and 5-aryl ...
A. N. Thakore +2 more
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Reaction of vinyl azides with nitrosyl tetrafluoroborate yields 1,2,5-oxadiazoles and 1,2,4-oxadiazoles depending on the structure of the azide. Reaction of 1,2-dialkyl vinyl azides with nitryl tetrafluoroborate gives 2-oxo-1,2,5-oxadiazoles in high yields whereas 1-aryl-2-alkyl vinyl azides gave moderate yields of 3-aryl-1,2,5-oxadiazoles and 5-aryl ...
A. N. Thakore +2 more
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Computational Study on the Vinyl Azide Decomposition
The Journal of Physical Chemistry A, 2014The decomposition mechanism of vinyl azide (CH2CHN3) has been studied by calculations of the electronic structure. In addition, a study based on the topology of the electron charge density distribution and its Laplacian function, within the Quantum Theory of Atoms in Molecules (QTAIM), has been carried out with the aim of comprehending the electron ...
Darío J R, Duarte +2 more
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