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Amide Synthesis by Nucleophilic Attack of Vinyl Azides

Angewandte Chemie - International Edition, 2014
AbstractA 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.
Xu Zhu, Yi-Feng Wang, Shunsuke Chiba
exaly   +4 more sources

Reactions of Vinyl Azides

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 ...
exaly   +2 more sources

New Methods for the Synthesis of Vinyl Azides

Angewandte Chemie International Edition in English, 1971
AbstractA 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
exaly   +2 more sources

Indium(III) Catalyzed Reactions of Vinyl Azides and Indoles

Organic Letters, 2020
Indium 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
Alex M Szpilman, Atul Ashok More
exaly   +3 more sources

Triplet Sensitized Photolysis of a Vinyl Azide: Direct Detection of a Triplet Vinyl Azide and Nitrene

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
openaire   +7 more sources

Electron‐Catalyzed Fluoroalkylation of Vinyl Azides

Chemistry – A European Journal, 2016
AbstractThe 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
openaire   +2 more sources

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