Chrétien-Longi reaction

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The Chrétien-Longi reaction is a name reaction in organic chemistry . The reaction was first reported in 1944 by André Chrétien and Yves Longi.

Overview reaction

In the Chrétien-Longi reaction, an ester of nitrous acid is synthesized from an alcohol with the help of sodium nitrite and aluminum sulfate .

ChretienLongi overview V1.svg

Reaction mechanism

In the proposed reaction mechanism , the alcohol is reacted with sodium nitrite . This is followed by protonation and the desired ester is created.

ChretienLongi mechanism V3.svg

modification

The reaction can also be carried out with dilute acetic acid .

application

The Chrétien-Longi reaction is used for the synthesis of esters of nitrous acid.

Individual evidence

  1. a b c d e Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 639-641 , doi : 10.1002 / 9780470638859 .
  2. a b c Jack Tadanier, Wayne Cole: Configurational Assignment to C-6 Epimeric 3 α, 5α- Cyclosteroid Alcohols and Amines by Means of Nmr In: The Journal of Organic Chemistry . tape 27 , no. December 12 , 1962, p. 4610-4615 , doi : 10.1021 / jo01059a115 .