I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Diethyl cyanomethyl phosphonate is used as an intermediate in Horner-Emmons reaction for the synthesis of substituted nitriles and their amide and heterocyclic derivatives. It is known as a modified Wittig reagent used in the preparation of alpha, beta-unsaturated nitriles from ketones or aldehydes like 3-hydroxy-3-methylbutanal. It reacts with epoxides and nitrones to prepare cyano-substituted cyclopropanes and aziridines respectively. It is actively involved in the synthesis of alpha-arylated alkanenitriles via reaction with aryl iodides in presence of CuI.
Horner-Wadsworth-Emmons olefination converts carbonyl compounds to substituted acrylonitriles: J. Am. Chem. Soc., 83, 1733 (1961); J. Org. Chem., 30, 505 (1965). LiOH has been found to be an effective base for this reaction: Tetrahedron Lett., 44, 1333 (2003). See Appendix 1. See also 3-Coumaranone, A10202.
The active methylene group can be monoalkylated under phase transfer conditions with alkyl iodides or allylic or benzylic bromides: Synthesis, 516 (1975). Use of alumina as base leads predominantly to the Knoevenagel product rather than the Wadsworth-Emmons: Tetrahedron, 41, 1259 (1985).
Grun, A.; Balint, E.; Keglevich, G. Solid-Liquid Phase C-Alkylation of Active Methylene Containing Compounds under Microwave Conditions. Catalysts 2015, 5 (2), 634-652.
Dai, Y.; Yu, B. Total synthesis of astrosterioside A, an anti-inflammatory asterosaponin. Chem. Commun. 2015, 51 (72), 13826-13829.
Gefahrenhinweise (EU): H302-H312-H331-H315-H319
Harmful if swallowed. Harmful in contact with skin. Toxic if inhaled. Causes skin irritation. Causes serious eye irritation.
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.