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Waste-free chemistry of diazonium salts and benign separation of coupling products in solid salt reactions

机译：重氮盐的无废化学和固体盐反应中偶联产物的良性分离

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Gas-solid and solid-solid techniques allow for waste-free and quantitative syntheses in the chemistry of diazonium salts. Five techniques for diazotations with the reactive gases NO2 NO and NOCl are studied. Two types are mechanistically investigated with atomic force microscopy (AFM) and are interpreted on the basis of known crystal packings. The same principles apply to the cascade reactions that had been derived from one-step reactions. Solid diazonium salts couple quantitatively with solid diphenylamine and anilines to give the triazenes. Azo couplings are achieved with quantitative yields by cautious co-grinding of solid diazonium salts with beta-naphthol and C-H acidic heterocycles, such as barbituric acids or pyrazolinones. Solid diazonium salts may be more easily applied in a stoichiometric ratio for couplings in solution. Co-grinding of solid diazonium salts with KI gives quantitative yields of various solid aryl iodides. The unavoidable coupling products in salt reactions are completely separated from the insoluble products in a highly benign manner. The solid-state reactions compare favourably with similar solution reactions that produce much waste. The structures of the products are elucidated with IR and NMR spectroscopy and mass spectrometry. while the tautomeric properties of the compounds are studied with density functional calculations at the B3LYP/6-31G* and BLYP/6-31G** levels. [References: 51]
机译：气固和固固技术可在重氮盐的化学反应中实现无浪费的定量合成。研究了用反应性气体NO2 NO和NOCl重氮化的五种技术。两种类型通过原子力显微镜（AFM）进行了机械研究，并根据已知的晶体堆积进行了解释。相同的原理适用于源自一步反应的级联反应。固体重氮盐与固体二苯胺和苯胺定量偶合，得到三氮烯。通过将固体重氮盐与β-萘酚和C-H酸性杂环（如巴比妥酸或吡唑啉酮）进行谨慎的共研磨，可以定量获得偶氮偶联。固体重氮盐可以更容易以化学计量比应用于溶液中的偶联。固体重氮盐与KI的共研磨给出了各种固体芳基碘化物的定量收率。盐反应中不可避免的偶合产物以高度良性的方式与不溶性产物完全分离。固态反应与产生大量废物的类似溶液反应相比具有优势。产物的结构通过IR和NMR光谱法和质谱法阐明。同时通过B3LYP / 6-31G *和BLYP / 6-31G **水平的密度泛函计算研究了化合物的互变异构性质。 [参考：51]

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