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Azo Coupling Reactions of Aliphatic Diazonium Ions and Related Processes

1 Azo Coupling Reactions of Aliphatic Diazonium Ions and Related Processes [Pg.191]

Diazo Chemistry II Aliphatic, Inorganic and Organometallic Compounds. By Heinrich Zollinger Copyright 1995 VCH Verlagsgesellschaft mbH ISBN 3-527-29222-5 [Pg.191]

The first azo coupling products of simple (i. e., not bridgehead) compounds were detected by Nesnow and Shapiro (1969), when they allowed l,2-dihydro-6-hydroxy-pyridin-2-one (6.3) to react with a large excess of diazomethane (1 100) in ether. They isolated l,2,3,6-tetrahydro-l-methyl-2,6-dioxopyridine-3-one methylhydrazone (6.4) in addition to the expected products of N- and O-methylation (6-2). [Pg.192]

An analogous result was reported by Testaferri et al. (1975) for the reaction of diazoethane with the thieno[3,2-Z ]thiophene derivative 6.5, where 011-ethylation and azo coupling in 3-position are observed. [Pg.192]

Nesnow and Shapiro and Testaferri et al. assume that the diazoalkanes are first protonated, in the case of l,2-dihydro-6-hydroxypyridin-2-one by the proton of the hydroxy group, with the thienothiophene derivative due to the tautomerism 6.5 6.6, i.e., by one of the protons of the methylene groups in 3- and 5-position of 6.5 and 6.6, and the formation of an intermediate ion pair of type 6.7. [Pg.192]




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Aliphatic Diazonium Ions

Azo coupling

Coupled processes

Coupling of reactions

Coupling processes

Diazonium coupling

Diazonium ions coupling

Diazonium ions reaction

Diazonium ions, and

Diazonium reaction

Ion coupling

Ion coupling reactions

Ion process

Process of reaction

Reaction of ions

Reactions, coupled and

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