117738-78-0Relevant articles and documents
Synthesis of Azaylide-Based Amphiphiles by the Staudinger Reaction
Kishida, Natsuki,Suzuki, Hayate,Toyota, Shinji,Yamashina, Masahiro,Yoshizawa, Michito
, p. 17915 - 17919 (2021)
Catalyst- and reagent-free reactions are powerful tools creating various functional molecules and materials. However, such chemical bonds are usually hydrolysable or require specific functional groups, which limits their use in aqueous media. Herein, we report the development of new amphiphiles through the Staudinger reaction. Simple mixing of chlorinated aryl azide with a hydrophilic moiety and various triarylphosphines (PAr3) gave rise to azaylide-based amphiphiles NPAr3, rapidly and quantitatively. The obtained NPAr3 formed ca. 2 nm-sized spherical aggregates (NPAr3)n in water. The hydrolysis of NPAr3 was significantly suppressed as compared with those of non-chlorinated amphiphiles nNPAr3. Computational studies revealed that the stability is mainly governed by the decrease in LUMO around the phosphorus atom owing to the o-substituted halogen groups. Furthermore, hydrophobic dyes such as Nile red and BODIPY were encapsulated by the spherical aggregates (NPAr3)n in water.
Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells
Meguro, Tomohiro,Terashima, Norikazu,Ito, Harumi,Koike, Yuka,Kii, Isao,Yoshida, Suguru,Hosoya, Takamitsu
supporting information, p. 7904 - 7907 (2018/07/25)
Efficient formation of water- and air-stable aza-ylides has been achieved using the Staudinger reaction between electron-deficient aromatic azides such as 2,6-dichlorophenyl azide and triarylphosphines. The reaction proceeds rapidly and has been successfully applied to chemical modification of proteins in living cells.
Pesticidal compounds
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, (2008/06/13)
Bicyclooctane pesticides of the formula are prepared by cyclisation of In these formulae R may be various organic groups and is preferably n-butyl or n-propyl while R2 is a polysubstituted phenyl group.