ChemInform Abstract: Michael Addition of Phosphorus-Substituted CH-Acids under Phase-Transfer Conditions.

✍ Scribed by E. A. TARASENKO; P. MUKHAIIMANA; A. V. TSVETKOV; N. V. LUKASHEV; I. P. BELETSKAYA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199832225

✦ Synopsis

Addition of Phosphorus-Substituted CH-Acids under Phase-Transfer Conditions.

-Phosphonoacetic acid (I) is shown to undergo Michael addition to various activated olefins under phase-transfer conditions. 1:1 or 1:2 Adducts are formed depending on the electronic structure of the olefins and the molar ratio of reactants. Temperature, nature of the base as well as the presence of an ammonium salt catalyst only effects the yields but not selectivity. An analogous behavior is observed in the reaction of tetraethyl methylidenediphosphonate (VII) with olefins although its lower CH-acidity causes reduced yields.