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Reduction and Hydrocyanation of Aziridines with C‐C Bond Cleavage
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-29 , DOI: 10.1002/ejoc.202400613
Yuki Kawamoto 1 , Tomoyuki Yoshimura 2 , Jun-ichi Matsuo 3
Affiliation  

The carbon‐carbon bond in three‐membered ring of 2,3‐diaryl aziridines was reductively cleaved to give the corresponding dibenzylamine derivatives by electrocyclic ring opening of N‐Li or N‐Na aziridines followed by reduction of the 2‐azaallyl anion formed with sodium borohydride in ethanol. Hydrocyanation of the 2‐azaallyl anion with trimethylsilyl cyanide gave a secondary amine bearing a cyano group at the benzylic position. The effects of substituents on the electrocyclic ring opening of N‐Li aziridines were also clarified.

中文翻译:


C-C 键断裂的氮丙啶还原和氢氰化



通过 N-Li 或 N-Na 氮丙啶的电环开环,然后还原形成的 2-氮杂烯丙基阴离子,2,3-二芳基氮丙啶三元环中的碳-碳键被还原断裂,得到相应的二苄胺衍生物。硼氢化钠的乙醇溶液。 2-氮杂烯丙基阴离子与三甲基氰硅烷进行氢氰化,得到在苄基位置带有氰基的仲胺。取代基对 N-Li 氮丙啶电环开环的影响也得到了阐明。
更新日期:2024-06-29
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