Phosphorus, Sulfur and Silicon and the Related Elements p. 433 - 445 (2007)
Update date:2022-08-11
Topics:
Hayashi, Masahiko
Kawabata, Hirotoshi
Yoshimoto, Kazuya
Tanaka, Takanori
We have focused on the basicity of Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) in organic synthesis. To extend the utility of TTMPP, we examined the reaction of α,β-unsaturated aldehydes with trimethylsilyl cyanide in the presence of TTMPP. Furthermore, to clarify the basic character of TTMPP, we measured 31P NMR of TTMPP and related compounds. First, the reaction of cinnamaldehydes with trimethylsilyl cyanide in the presence of a catalytic amount of TTMPP afforded the corresponding saturated carboxylic acids after hydrolysis with 1M HCl. Treatment of the reaction mixture with alcohols or amines instead of 1M HCl gave the corresponding saturated esters and amides, respectively. As a result of studies of the reaction mechanism, it was revealed that the reaction proceeded via silylcyanation of α,β-unsaturated aldehydes with trimethylsilyl cyanide to produce trimethylsilyl ethers of cyanohydrin and subsequent isomerization that formed α-trimethylsiloxy vinyl cyanides, which were hydrolyzed to give saturated carboxylic acids. Copyright Taylor & Francis Group, LLC.
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