63777-68-4Relevant articles and documents
Stereoselective radical azidooxygenation of alkenes
Zhang, Bo,Studer, Armido
supporting information, p. 4548 - 4551 (2013/09/24)
Radical azidooxygenation of various alkenes is described. A readily prepared N3-iodine(III) reagent acts as a clean N3-radical precursor. Radical generation is achieved with TEMPONa acting as a mild organic reducing reagent. The C-radical generated after N3-radical addition is efficiently trapped by in situ generated TEMPO. Yields are good to excellent, and for cyclic systems azidooxygenation occurs with excellent diastereoselectivity.
A Novel Selective Route to 1-Substituted Benzotriazoles via Lithiation of Simple 1-Alkylbenzotriazoles
Katritzky, Alan R.,Wu, Jing,Kuzmierkiewicz, Wojciech,Rachwal, Stanislaw
, p. 1 - 6 (2007/10/02)
1-Methylbenzotriazole (2a) is lithiated readily with butyllithium or LDA at the methyl group to 4 and the subsequent reaction with various electrophiles provides 1-substituted benzotriazoles 5.Other 1-(n-alkyl)benzotriazoles 2 also undergo lithiation with LDA, the carbanions can be trapped with alkyl halides giving benzotriazoles 6 bearing secondary alkyl groups on the N-1 atom.On standing in the absence of electrophiles, all the lithium derivatives decompose to afford complex mixtures. - Key Words: Benzotriazoles, 1-alkyl / Lithiation / Haloalkanes
Reactions of 1-(α-Alkoxyalkyl)- and 1-(α-(Aryloxy)alkyl)benzotriazoles with the Grignard Reagents. A New and Versatile Method for the Preparation of Ethers
Katritzky, Alan R.,Rachwal, Stanislaw,Rachwal, Bogumila
, p. 6022 - 6029 (2007/10/02)
1-(α-Alkoxyalkyl)benzotriazoles deriving from aldehydes (other than formaldehyde), or from ketones, react with Grignard reagents at 110 deg C to provide a high-yielding, general synthesis of dialkyl and aryl ethers.Under similar conditions, 1-(alkoxymethyl)- and 1-((aryloxy)methyl)benzotriazoles give, by a different cleavage pattern of the N-C-O grouping, 1-alkylbenzotriazoles and N,N'-dialkyl-o-phenylenediamines.The 1-(α-alkoxyalkyl)benzotriazoles are easily prepared: (a) by condensation of benzotriazole, an aldehyde, and an alcohol under water-removing conditions; (b) by condensation of a 1-(α-chloroalkyl)benzotriazole with a sodium or potassium alkoxide or aryloxide; and (c) by condensatioon of an acetal or a ketal with benzotriazole.All the 1-(α-alkoxyalkyl)benzotriazoles and dialkyl or alkyl aryl ethers obtained were fully characterized by their 1H and 13C NMR spectra.