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.
Triethyl phosphonoacetate serves as a reactant used in Horner-Wadsworth-Emmons reactions, Tsuji-Trost type reactions, Intramolecular Heck-type cyclization and isomerizations and Intramolecular aryne-ene reactions. In Horner-Wadsworth-Emmons reaction, it is utilized as a reagent to prepare chiral 2-methylcyclopropanecarboxylic acid from (S)-propylene oxide.
Wadsworth-Emmons (Horner) reaction with aldehydes and ketones gives acrylic esters. See, e.g.: Org. Synth. Coll., 5, 509, 547 (1973), and Appendix 1.
Base-catalyzed aldol, Cannizzaro and saponification reactions can be minimized, by the use of, e.g.: K2CO3: Synthesis, 300 (1983); Tetrahedron Lett., 26, 53 (1985); F-: Tetrahedron Lett., 21, 2161 (1980); N-ethyldiisopropylamine + LiCl: Tetrahedron Lett., 25, 2183 (1984); Et3N + Li halides: J. Org. Chem., 50, 2624 (1985).
Reaction with aqueous formaldehyde does not lead to the "expected" Wadsworth-Emmons product, but to ethyl ɑ-(hydroxymethyl)acrylate, a precursor of the synthetically useful ethyl ɑ-bromomethylacrylate, by condensation with the initially-formed "aldol" product: Org. Synth. Coll., 8, 265 (1993).
Kim, H.; Paik, Y. K. Synthesis of Photoaffinity-Labeled Daumone Analogs. Bull. Korean Chem. Soc. 2015, 36 (9), 2177-2178.
Lee, J. Y.; Choi, J. H.; Ryoo, K. S.; Kwon, Y. B.; Hong, Y. P. Economical Synthesis of Grapevine Moth Sex Pheromone. Bull. Korean Chem. Soc. 2015, 36 (1), 421-423.
Gefahrenhinweise (EU): H315-H319
Causes skin irritation. Causes serious eye irritation.
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves. 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.