Zincke nitriding

Theodor Zincke (1843–1928)

The Zincke nitration is a name reaction from the field of organic chemistry and was first observed in 1900 by the German chemist Theodor Zincke (1843–1928). In this case, an electrophilic substitution takes place on the bromine substituent or iodine substituent in ortho or para position to the hydroxide substituent by a nitro group ; nitrophenols are formed .

Overview reaction

The Zincke nitration is carried out with nitrous acid .

The halogen (X = Br or iodine) is replaced by the new nitro group during the reaction. The radicals R and R ¹ can stand for methyl groups , methoxy groups or simply hydrogen .

Possible mechanism

The mechanism of the Zincke nitration is explained using an electrophilic aromatic substitution of nitrous acid on bromine-substituted cresols. One of the bromine substituents is substituted, which is then split off as hydrogen bromide by deprotonation . The exact mechanism of the reaction is not clear.

application

Zincke nitration is useful in preparation for the production of 2-nitrophenols and 4-nitrophenols, respectively.

literature

Zerong Wang: Comprehensive Organic Name Reactions and Reagents. 1st edition. John Wiley & Sons, New Jersey 2009, ISBN 978-0-471-70450-8 , pp. 3168-3171.
Martha Windholz: The Merck Index. 9th edition. Merck & Co., New Jersey 1976, ISBN 0-911910-26-3 , p. 98.
Theodor Zincke, On the action of nitrous acid on bromine and chlorine derivatives of phenols , J. Prakt. Chem. 1900, Volume 61: pp. 561-567 and correction by J. Prakt. Chem. 1900, Volume 63: p. 183 ff , add. Correction in Liebigs Ann. 328: 264-265 (1903). - doi : 10.1002 / prac.19000610145

Individual evidence

^ Zerong Wang: Comprehensive Organic Name Reactions and Reagents. 1st edition. John Wiley & Sons, New Jersey 2009, ISBN 978-0-471-70450-8 , pp. 3168f.

^ ^A ^b Zerong Wang: Comprehensive Organic Name Reactions and Reagents. 1st edition. John Wiley & Sons, New Jersey 2009, ISBN 978-0-471-70450-8 , p. 3169.

↑ Theodor Zincke, On the action of nitrous acid on bromine and chlorine derivatives of phenols , J. Prakt. Chem. 1900, Volume 61: p. 562.

[ZW-1] Zerong Wang: Comprehensive Organic Name Reactions and Reagents. 1st edition. John Wiley & Sons, New Jersey 2009, ISBN 978-0-471-70450-8 , pp. 3168f.

[ZW2-2] A ^b Zerong Wang: Comprehensive Organic Name Reactions and Reagents. 1st edition. John Wiley & Sons, New Jersey 2009, ISBN 978-0-471-70450-8 , p. 3169.