Dutt-Wormall reaction

The Dutt-Wormall reaction is a name reaction in organic chemistry published in 1921 by Pavitra Kumar Dutt, Hugh Robinson Whitehead and Arthur Wormall . This reaction describes the synthesis of aromatic azides .

Overview reaction

In the Dutt-Wormall reaction, an aromatic azide is produced from a diazonium salt in several reaction steps:

Reaction mechanism

In the proposed reaction mechanism, the cation of the diazonium salt 1 is first attacked by a sulfonamide 2 . After a proton has been split off, the aromatic diazoaminosulfinate 3 is formed . The hydrolysis by a hydroxide ion and subsequent splitting off of sulfonic acid leads to azide 4 :

application

This reaction is used to make aromatic azides.

Individual evidence

^ Pavitra Kumar Dutt, Hugh Robinson Whitehead , Arthur Wormall: CCXLI. — The action of diazo-salts on aromatic sulphonamides. Part I . In: J. Chem. Soc., Trans. Volume 119 , no. 0 , 1921, p. 2088-2094 , doi : 10.1039 / CT9211902088 .
^ ^A ^b Namboothiri, I. (Irishi): Organic syntheses based on name reactions: a practical guide to 750 transformations . 3rd ed.Elsevier, Amsterdam 2012, ISBN 978-0-08-096631-1 , pp. 134 .
↑ ^a ^b ^c Wang, Zerong (Daniel Zerong): Comprehensive organic name reactions and reagents . John Wiley, Hoboken, NJ 2009, ISBN 978-0-471-70450-8 , pp. 946-948 .

[1] Pavitra Kumar Dutt, Hugh Robinson Whitehead , Arthur Wormall: CCXLI. — The action of diazo-salts on aromatic sulphonamides. Part I . In: J. Chem. Soc., Trans. Volume 119 , no. 0 , 1921, p. 2088-2094 , doi : 10.1039 / CT9211902088 .

[:0-2] A ^b Namboothiri, I. (Irishi): Organic syntheses based on name reactions: a practical guide to 750 transformations . 3rd ed.Elsevier, Amsterdam 2012, ISBN 978-0-08-096631-1 , pp. 134 .

[:1-3] Wang, Zerong (Daniel Zerong): Comprehensive organic name reactions and reagents . John Wiley, Hoboken, NJ 2009, ISBN 978-0-471-70450-8 , pp. 946-948 .