- One-Pot Catalytic Synthesis of gem-Diazides and Their Direct Conversion into Safe Materials
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Commercial availability and storage issues have left reactivity studies of gem-diazides underdeveloped, in contrast to the relatively abundant chemistry of monoazides. The present study uses triflic acid (0.1 mol-%) as a catalyst for the quantitative prod
- Samuel, Prinson P.,Kundu, Subrata,Mohapatra, Chandrajeet,George, Anjana,De, Susmita,Parameswaran, Pattiyil,Roesky, Herbert W.
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- Trapping of azidocarbenium ion: A unique route for azide synthesis
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For the first time, a sensitive azidocarbenium ion intermediate has been trapped with various nucleophiles to provide azides in excellent chemoselectivity. This provides a novel approach for the chemoselective synthesis of primary and secondary benzyl azides from aldehydes in a one-pot reaction. Enantioselective nucleophilic addition to the azidocarbenium ion has also been initiated.
- Pramanik, Suman,Ghorai, Prasanta
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supporting information
p. 2104 - 2107
(2014/05/06)
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- Chemoselective three-component synthesis of homoallylic azides using an FeCl3 catalyst
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A one-pot, three-component synthesis of homoallylic azides from corresponding aldehydes, TMS-allyl, and TMS-N3 has been developed for the first time using an FeCl3 catalyst. The aromatic and hetero-aromatic aldehydes provided the cor
- Pramanik, Suman,Ghorai, Prasanta
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p. 23157 - 23165
(2013/11/19)
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- Indium(III) triflate catalyzed tandem azidation/1,3-dipolar cycloaddition reaction of ω,ω-dialkoxyalkyne derivatives with trimethylsilyl azide
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The azidation reaction of dialkyl acetal derivatives with trimethylsilyl azide (TMSN3) was efficiently catalyzed by 1-5 mol % of In(OTf) 3. The major product differed depending on the substrate structure and molar ratio of TMSN3
- Yanai, Hikaru,Taguchi, Takeo
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p. 8639 - 8643
(2007/10/03)
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- Spontaneous cleavage of gem-diazides: A comparison of the effects of α-azido and other electron-donating groups on the kinetic and thermodynamic stability of benzyl and alkyl carbocations in aqueous solution
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The solvolysis reactions of ring-substituted benzylic and 1-propyl gem-diazides in water proceed by a stepwise mechanism through α-azido carbocation intermediates, which are captured by water to give the corresponding aldehyde as the sole detectable produ
- Richard, John P.,Amyes, Tina L.,Jagannadham, Vandanapu,Lee, Yong-Gu,Rice, Douglas J.
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p. 5198 - 5205
(2007/10/02)
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- TiCl4-Catalyzed Addition of HN3 to Aldehydes and Ketones. Thermolysis and Photolysis of α-Azido Ethers
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Aldehydes react with hydrazoic acid and alcohols in the presence of catalytic amounts of TiCl4 to produce α-azido ethers.The conversion of simple ketones to methyl α-azido alkyl ethers can be accomplished by means of hydrazoic acid and methyl orthoformate.Both gas-phase thermolysis and photolysis of representative α-azido ethers were studied and shown to produce mainly imino ethers.In the thermolysis, migratory preference decreases in the series H >> CH3 > Ph >> OR.
- Hassner, Alfred,Fibiger, Richard,Amarasekara, Ananda S.
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- REACTIONS OF TRIMETHYLSILYL AZIDE WITH ALDEHYDES: FACILE AND CONVENIENT SYNTHESES OF DIAZIDES, TETRAZOLES, AND NITRILES
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The reactions of trimethylsilyl azide (TMSA) with various aldehydes were found to be versatile procedures for the synthesis of gem- and 1,3-diazides, tetrazoles, and nitriles, whose formation was varied by controlling the quantities of TMSA, catalyst, and the reaction conditions.
- Nishiyama, Kozaburo,Oba, Makoto,Watanabe, Akio
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p. 693 - 700
(2007/10/02)
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