62249-35-8Relevant articles and documents
Reactions of Sodium Diisopropylamide: Liquid-Phase and Solid-Liquid Phase-Transfer Catalysis by N, N, N′, N″, N″-Pentamethyldiethylenetriamine
Algera, Russell F.,Collum, David B.,Ma, Yun,Woltornist, Ryan A.
supporting information, p. 13370 - 13381 (2021/09/03)
Sodium diisopropylamide (NaDA) in N,N-dimethylethylamine (DMEA) and DMEA-hydrocarbon mixtures with added N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDTA) reacts with alkyl halides, epoxides, hydrazones, arenes, alkenes, and allyl ethers. Comparisons of PMDTA with N,N,N′,N′-tetramethylethylenediamine (TMEDA) accompanied by detailed rate and computational studies reveal the importance of the trifunctionality and κ2-κ3 hemilability. Rate studies show exclusively monomer-based reactions of 2-bromooctane, cyclooctene oxide, and dimethylresorcinol. Catalysis with 10 mol % PMDTA shows up to >30-fold accelerations (kcat > 300) with no evidence of inhibition over 10 turnovers. Solid-liquid phase-transfer catalysis (SLPTC) is explored as a means to optimize the catalysis as well as explore the merits of heterogeneous reaction conditions.
Sodium Diisopropylamide in N,N-Dimethylethylamine: Reactivity, Selectivity, and Synthetic Utility
Ma, Yun,Algera, Russell F.,Collum, David B.
, p. 11312 - 11315 (2016/11/29)
The reactivities and chemoselectivities of sodium diisopropylamide (NaDA) in N,N-dimethylethylamine (DMEA) are compared with those of lithium diisopropylamide (LDA) in tetrahydrofuran (THF). Metalations of arenes, epoxides, ketones, hydrazones, dienes, and alkyl and vinyl halides are represented. The positive attributes of NaDA-DMEA include high solubility, stability, resistance to solvent decomposition, and ease of preparation. The high reactivities and chemoselectivities often complement those of LDA-THF.
Efficient photocatalytic oxidation of cycloalkenes by dihydroxo(tetraphenylporphyrinato)-antimony supported on silica gel under visible light irradiation
Shiragami, Tsutomu,Makise, Ryu-Ichi,Inokuchi, Yousuke,Matsumoto, Jin,Inoue, Haruo,Yasuda, Masahide
, p. 736 - 737 (2007/10/03)
In order to develop a photocatalyst operating under visible light irradiation, silica gel-supported dihydroxo(tetraphenylporphyrinato)antimony (V) complex, [SbTPP(OH)2]+/SiO2, was prepared. The photocatalytic oxidation of cycloalkenes with oxygen molecule was performed on [SbTPP(OH)2]+/SiO2 particles under irradiation of fluorescent light. The photocatalytic oxidation of cycloalkenes gave the corresponding cis-1,2-epoxycycloalkane, 2-cycloalkene-1-ol, and trans-1,2-cycloalkanediol.