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シュタウディンガー反応 .
シュタウディンガー反応 (シュタウディンガーはんのう、Staudinger reaction)とは、有機合成 反応のひとつ。アジド とホスフィン (または亜リン酸エステル)が作用するとイミノホスホランを生じる反応(下式1)のこと[1] [2] 。発明者のヘルマン・シュタウディンガー にその名をちなんでいる。
イミノホスホランはアザイリドとも呼ばれ、加水分解 によりアミン とホスフィンオキシドに変わる(下式2)。シュタウディンガー反応を鍵反応とした、アジドからアミンへの還元反応はシュタウディンガー還元 と呼ばれる。アザイリドはまた、アルデヒドと反応してイミンを与える(アザ-ウィッティヒ反応、下式3)。ホスフィンとしては通常トリフェニルホスフィン が用いられ、反応後にはトリフェニルホスフィンオキシド に変わる。
R
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⟶
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{\displaystyle {\ce ((R-N3}+ P(C6H5)3 -> R-N=P(C6H5)3))}
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{\displaystyle {\ce ((R-N=P(C6H5)3}+ H2O -> {R-NH2}+ O=P(C6H5)3))}
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{\displaystyle {\ce ((R-N=P(C6H5)3}+ R'CHO -> R-N=CHR'))}
反応機構は、ホスフィンのリン原子がアジドの末端窒素に求核攻撃・付加し、4員環中間体を経て窒素を脱離させながらイミンを与えると考えられている。
シュタウディンガー反応の機構
^ Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919 , 2, 635. DOI: 10.1002/hlca.19190020164
^ 総説: Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981 , 37 , 437-472. DOI: 10.1016/S0040-4020(01)92417-2
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