76599-46-7Relevant academic research and scientific papers
Oxidative nitrene transfer from azides to alkynes via Ti(ii)/Ti(iv) redox catalysis: Formal [2+2+1] synthesis of pyrroles
Pearce, Adam J.,See, Xin Yi,Tonks, Ian A.
supporting information, p. 6891 - 6894 (2018/06/26)
Catalytic oxidative nitrene transfer from azides with the early transition metals is rare, and has not been observed without the support of redox noninnocent spectator ligands. Here, we report the formal [2+2+1] coupling of azides and alkynes via TiII/TiIV redox catalysis from simple Ti halide imido precatalysts. These reactions yield polysubstituted N-alkyl pyrroles, including N-benzyl protected pyrroles and rare examples of very electron rich pentaalkyl pyrroles. Mechanistic analysis reveals that [2+2+1] reactions with bulky azides have different mechanistic features from previously-reported reactions using azobenzene as a nitrene source.
Synthesis of Adamantane Derivatives. 52. 1,3-Dipolar Cycloaddition Reactions of 1-Azidoadamantane. Reactivity, Regioselectivity, and Carbon-13 Nuclear Magnetic Resonance Spectra of 1-(1-Adamantyl)-Δ2-1,2,3-triazolines and -1H-1,2,3-triazoles
Sasaki, Tadashi,Eguchi, Shoji,Yamaguchi, Mikio,Esaki, Toshiyuki
, p. 1800 - 1804 (2007/10/02)
The 1,3-dipolar cycloadditions of 1-azidoadamantane (1) with various olefinic and acetylenic dipolarophiles are described.As olefinic dipolarophiles, strained olefins such as 2-5 and electron-poor olefins such as 11,12,15, and 18 gave the corresponding ad
