The effects of phosphorus substituents on the reactivity of α‐alkoxyphosphonium salts with nucleophiles has been explored. Reactions of α‐alkoxyphosphonium salts, prepared from various acetals and tris(o‐tolyl)phosphine, with a variety of nucleophiles proceeded efficiently. These processes represent the first examples of high‐yielding nucleophilic substitution reactions of α‐alkoxyphosphonium salts
The structure and electronic nature of the phosphine have a significant influence on not only the formation, but also the subsequent transformation of O,P-acetals. The O,P-acetals generated from tris(o-tolyl)phosphine [(o-tol)3P] underwent efficient substitution reactions with various nucleophiles.
AOYAMA, TOYOHIKO;SHIOIRI, TAKAYUKI, TETRAHEDRON LETT., 31,(1990) N8, C. 5507-5508
作者:AOYAMA, TOYOHIKO、SHIOIRI, TAKAYUKI
DOI:——
日期:——
Trimethylsilyldiazomethane : a convenient reagent for the o-methylation of alcohols
作者:Toyohiko Aoyama、Takayuki Shioiri
DOI:10.1016/s0040-4039(00)97884-5
日期:1990.1
Trimethylsilyldiazomethane smoothly reacts with alcohols in dichloromethane in the presence of 42% aqueous fluoroboric acid to give methyl ethers in good to high yields.