α,β-Unsaturated Carboxylic Acid Derivatives. X. The Synthesis and Reaction of α-Azido-diethoxyphosphinyl-α- and β-alkenes
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概要
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α,β-Dibromo-β-diethoxyphosphinylalkane (<B>2</B>) was obtained as a stereo-isomeric mixture (erythro : threo=50 : 50) by the bromination of β-diethoxyphosphinyl-α-alkene, composed of the <I>E</I>-isomer and the <I>Z</I>-isomer (50 : 50). It was found that the reaction of <B>2</B> with sodium azide proceeded stereoselectively to give only the. <I>E</I>-isomer of α-bromo-β-diethoxyphosphinyl-α-alkene, which could then be converted into α-azido-β-diethoxyphosphinyl-α-alkene (<B>4</B>), and α-azido-β-diethoxyphosphinyl-β-alkene, whose configuration was determined by the coupling constants between the phosphorus atom and the vinyl protons. Moreover, the irradiation of <B>4</B> yielded a new type of β-diethoxyphosphinyl-α-alkene-α-imine, which later rearranged into the corresponding nitrile.
- 公益社団法人 日本化学会の論文
著者
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Yonezawa Yasuchika
Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University
-
Sakamoto Hiroshi
Laboratory Of Biochemistry Department Of Chemistry Faculty Of Science Kyushu University
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Yoshimura Juji
Laboratorium für Organische Chemie Technische Hochschule Tokyo
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Shin Chung-gi
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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