20119-28-2Relevant academic research and scientific papers
Aryne formation from 1-(3′-Carboxyaryl)-3,3-dim ethyl trianzenes
Christopher Buxton,Heaney, Harry
, p. 3929 - 3938 (1995)
A study of the decomposition of 1-(2′-carboxyphenyl)-3,3-dimethyltriazene and the tetrabromoand tetrachloro- analogues showed that the arenediazonium-2-carboxylates were intermediates in the formation of the corresponding arynes: the 1-(2′-carboxyteirahalophenyl)-3,3-dimethyltriazenes are stable precursors that enable cycloaddition reactions of the tetrahalobenzynes to be carried out in acceptable yields using substrates such as N-methylpyrrole,p-xylene and m-dimethoxybenzene.
Reaction of benzyne with formamides and acetylimidazole
Okuma, Kentaro,Nojima, Akiko,Nakamura, Yuki,Matsunaga, Nahoko,Nagahora, Noriyoshi,Shioji, Kosei
experimental part, p. 328 - 332 (2011/05/14)
The reaction of DMF with o-trimethylsilylphenyl triflate in the presence of CsF afforded dimethyldiphenylammonium triflate, xanthene, and xanthone in 62%, 16%, and 24% yields, respectively. On the other hand, the reaction of dimethylthioformamide with triflate and CsF resulted in diphenyl sulfide, xanthene, and xanthone in 62%, 10%, and 12% yields, respectively. The reaction of acetylimidazole with benzyne gave 9-N,N-diphenylaminoanthracene in 85% yield.
Waste-Free Quantitative Gas/Solid Diazotation Using Nitrogen Dioxide and Triazene Synthesis, Both Avoiding Liquid Phases
Kaupp, Gerd,Herrmann, Andreas
, p. 256 - 260 (2007/10/03)
Solid diazonium nitrates (2a-j) are quantitatively obtained by reaction of crystalline anilines (1a-j) with gaseous nitrogen dioxide. Solid diazonium salts react quantitatively with dimethylamine to give the triazenes (4a-j). Wastes that are typical for the previous syntheses of these compounds in solution are avoided. Atomic force microscopic (AFM) investigations indicate long-range molecular movements due to phase rebuilding. The features thus formed are related to the known crystal structures of the starting anilines. The diazotations run to completion, because, after accumulation of product molecules, phase transformation to give the product lattices leads to crystal disintegration and thus to formation of fresh surface over and over.
AFM in organic solid state reactions
Kaupp, Gerd,Schmeyers, Jens,Haak, Michael,Marquardt, Thorsten,Herrmann, Andreas
, p. 315 - 317 (2007/10/03)
Organic solid-state reactions are probed with the atomic force microscope (AFM). In all cases phase rebuilding gives rise to characteristic submicroscopic features which change in shape due to phase transformation in later stages of the chemical reaction. Photo-(E/Z)-isomerization of olefin 1 occurs in the crystal, photodimerization of 9-chloroanthracene 3 is used as a probe for characterizing the luminosity distribution of SNOM-tips. Gas/solid imbibition in chiral host 5 proceeds enantiospecifically. Histidine crystals form the dihydrochloride with HCl, ammonia and methylamine react face-selectively with crystalline adipic acid 8, furane-2-carboxylic acid 10 and 2-mercaptobenzothiazole 12. Crystals of olefin 14 add chlorine. Solid-state diazotations and subsequent transformations of the solid diazonium nitrates into triazenes occur quantitatively. Solid/solid pinacol- and benzilic acid rearrangements are probed with the AFM. The features formed by long range molecular movements relate to the crystal packing and are thus different on different faces. Correlations with X-ray structural data are demonstrated. All reactions proceed to completion on a preparative scale and do not produce wastes as do their less selective counterparts if performed in solution. Organic solid-state reactions, AFM, SNOM-tip, imbibition, salt formations, chlorination, diazotations, triazene, gas/solid-reactions, solid/solid-reactions, crystal packing, waste-free reactions.
