SYNTHESE VON O-HYDROXYPHENYL-ALKOXYMETHYLSILANEN DURCH [1,3](O→C)-SILYLVERSCHIEBUNG Synthesis of o-Hydroxyphenyl-alkoxymethylsilanes via [1,3]-(O→C)-Silyl Migration

Abstract

o-Haloaryloxy-alkoxymethylsilanes o-XC₆H₄OSiR_n(OR′)_3-n react with sodium or magnesium by sonoactivation via metallation and [1,3]-(O→C)-silyl migration to the sodium or magnesium salts of the o-hydroxyphenyl-alkoxymethylsilanes. These can be protolyzed to the o-hydroxyphenyl-silanes o-HOC₆H₄SiR_n(OR′)_3-n or reacted with chlorosilanes, diesterchlorophosphates, 2-haloacetic esters or acylhalides to give corresponding derivatives in a one pot synthesis.

Key Words:

• Metallation
• [1,3]-(O→C)Silyl migration
• o-hydroxyphenyl-alkoxymethylsilanes
• silylethers
• ethers and esters of hydroxyphenylsilanes
• sonoactivation