Perkow reaction

The Perkow reaction is a name reaction from the field of organic chemistry , which is named after the German chemist Werner Perkow (1915–1994). It is used to convert ketones that are substituted with leaving groups in the α-position to vinyl phosphates with the help of phosphites .

Reaction mechanism

Many different mechanisms are proposed for the Perkow reaction. The mechanism presented here comes from the book " Comprehensive Organic Name Reactions and Reagents " by Zerong Wang. In the first step, the phosphite attacks the carbonyl group . This is followed by a rearrangement of the phosphorus group, so that the desired vinyl phosphate is finally released.

application

The Perkow reaction is used in the synthesis of the following insecticides:

literature

Zerong Wang: Comprehensive Organic Name Reactions and Reagents . 1st edition. tape 2 (3 volumes). John Wiley & Sons , Hoboken (New Jersey) 2009, ISBN 978-0-471-70450-8 , Perkow Reaction (Chapter 489), pp. 2168-2172 , doi : 10.1002 / 9780470638859.conrr489 .
R. Anliker, E. Beriger, M. Geiger, K. Schmid: About the synthesis of phosphamidon and its degradation in plants . In: Helvetica Chimica Acta . tape 44 , no. 6 , 1961, pp. 1622–1645 , doi : 10.1002 / hlca.19610440621 .

Individual evidence

↑ Alexander Senning: Elsevier's Dictionary of Chemoetymology . The Whys and Whences of Chemical Nomenclature and Terminology. 1st edition. Elsevier, Amsterdam · Oxford 2006, ISBN 0-444-52239-5 , pp. 301 ( limited preview in Google Book search).
↑ Werner Perkow, Klaus Ullerich, Friedrich Meyer: New phosphoric acid esters with pupil-narrowing effect . In: Natural Sciences . tape 39 , no. 15 , 1952, pp. 353 , doi : 10.1007 / BF00589945 .
↑ Werner Perkow: Reactions with alkyl phosphites . I. Commun .: rearrangements in the reaction with chloral and bromal. In: Chemical Reports . tape 87 , no. 5 , 1954, pp. 755-758 , doi : 10.1002 / cber.19540870521 .

[1] Alexander Senning: Elsevier's Dictionary of Chemoetymology . The Whys and Whences of Chemical Nomenclature and Terminology. 1st edition. Elsevier, Amsterdam · Oxford 2006, ISBN 0-444-52239-5 , pp. 301 ( limited preview in Google Book search).

[2] Werner Perkow, Klaus Ullerich, Friedrich Meyer: New phosphoric acid esters with pupil-narrowing effect . In: Natural Sciences . tape 39 , no. 15 , 1952, pp. 353 , doi : 10.1007 / BF00589945 .

[3] Werner Perkow: Reactions with alkyl phosphites . I. Commun .: rearrangements in the reaction with chloral and bromal. In: Chemical Reports . tape 87 , no. 5 , 1954, pp. 755-758 , doi : 10.1002 / cber.19540870521 .