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

Chemistry : a European Journal
G KauppJ Schmeyers

Abstract

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 NO(2), 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 spe...Continue Reading

References

Feb 1, 1976·Biochemical Pharmacology·T A ConnorsD E Wilman
Sep 1, 1967·Polski przeglad chirurgiczny·T F Lai, R E Marsh
Jan 1, 1982·Clinical and Experimental Dermatology·R M Mackie

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Citations

Oct 15, 2008·Journal of Molecular Recognition : JMR·Jie ShaoHuakuan Lin
Mar 4, 2017·The Journal of Organic Chemistry·Hanuman P KalmodeAtul C Chaskar
Nov 16, 2016·Physical Chemistry Chemical Physics : PCCP·Fei TongChristopher J Bardeen
Mar 6, 2010·Organic & Biomolecular Chemistry·Bernd SchmidtFrank Hölter
Oct 11, 2014·Chemistry : a European Journal·Takehiro HiraoTakeharu Haino
Feb 14, 2012·Langmuir : the ACS Journal of Surfaces and Colloids·Julia AgulloDaniel Bélanger

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