18166-02-4Relevant academic research and scientific papers
Formation and cycloaddition of nonstabilized N-unsubstituted azomethine ylides from (2-azaallyl)stannanes and (2-azaallyl)silanes
Pearson, William H.,Clark, Roger B.
, p. 4467 - 4471 (1999)
Protodestannylation or protodesilylation of (2-azaallyl)stannanes or (2- azaallyl)silanes led to the formation of nonstabilized N-unsubstituted azomethine ylides, which underwent cycloadditions with electron-poor alkenes to produce 2-alkyl- or 2,5-dialkyl
N,N′-bis(trimethylsilylmethyl)thiocarbamide and N,N′-bis(trimethylsilylmethyl)-λ6-thiocarbamide S,S-Dioxide
Vlasova,Grigor'eva,Voronkov
, p. 860 - 861 (2005)
N,N′-Bis(trimethylsilylmethyl)-λ6-thiocarbamide S,S-dioxide was synthesized by oxidation of N,N′-bis(trimethylsilylmethyl)thiocarbamide with hydrogen peroxide. The synthesized dioxide is a less active reducing agent than previously studied S,S-
Batch and Continuous-Flow One-Pot Processes using Amine Diazotization to Produce Silylated Diazo Reagents
Audubert, Clément,Gamboa Marin, Oscar Javier,Lebel, Hélène
supporting information, p. 6294 - 6297 (2017/05/19)
A novel synthesis of trimethylsilyldiazomethane (TMSCHN2) by diazotization of trimethylsilylmethylamine (TMSCH2NH2) is reported using batch and continuous flow synthesis. The latter affords a daily production of 275 g (2.4 mol) of TMSCHN2. Other silylated methylamines were also successfully reacted under the developed reaction conditions to furnish various silicon-bearing diazomethane reagents. The applicability of the process is highlighted by disclosure of batch and continuous flow one-pot esterification and 1,3-dipolar cycloaddition processes. Furthermore, the high-yielding esterification of carboxylic acids with silylated and substituted methylamines in continuous flow is disclosed. Finally, work-up and purification procedures are reported for the preparation of a 2-MeTHF solution of TMSCHN2, which can be used in rhodium-catalyzed methylenation and homologation reactions.
α-Alkyl-α-aminosilanes. 1. Metalation and alkylation between silicon and nitrogen
Sieburth, Scott McN.,Somers, Joseph J.,O'Hare, Heather K.
, p. 5669 - 5682 (2007/10/03)
tert-Butyl carbamate derivatives of readily available aminomethyltrialkylsilanes have been studied for their ability to undergo metalation between nitrogen and silicon, followed by reaction with an electrophile. Metalation is rapid and reaction with a variety of electrophiles proceeds efficiently. When a benzyl group is attached to nitrogen, benzylic deprotonation competes with deprotonation next to silicon.
Synthesis, Antitumor Activity, and Chemical Properties of Silaplatin and Related Platinum(II) and Platinum(IV) Complexes Derived from β-Silyl Amines
Anderson, Wayne K.,Kasliwal, Ravindra,Houston, D. Michael,Wang, Yueh-sha,Narayanan, Ven L.,et al.
, p. 3789 - 3797 (2007/10/03)
Platinum(II) and platinum(IV) coordination complexes derived from β-silyl-substituted amines were prepared.The solubility of selected complexes in water and physiological saline was measured, and the effect of the β-silicon on the reactivity of the complex in aqueous solution was determined by HPLC.The stabilities of selected silyl complexes were compared to the carbon analogues.The cyclic complexes 2a ("silaplatin") and its Pt(IV) analogue, 2b, were very active against L1210 leukemia in vivo.Both the platinum(II) complex 2a and the platinum(IV) complex 2b produced a significant number of cures over the dose range 10-40 mg/kg.The platinum(II) complex 2a, silaplatin, was very active in vivo against an L1210 leukemia subline that was resistant to cisplatin; 2a was also active, when given ip against ic implanted L1210.The cyclobutanedicarboxylic acid complex 3c was synthesized; this complex was active against both cisplatin sensistive and resistant L1210 leukemia but was less potent than the analogous dichloro compound 2a.The acyclic platinum(II) and platinum(IV) complexes 1a,b were synthesized and unexpectedly found to be inactive in vivo against L1210 leukemia.More lipophilic silaplatin analogues were prepared-Pt(II) complex 2c and Pt(IV) complex 2d have one additional methylene carbon compared to 2a,b, whereas Pt(II) complex 2e and Pt(IV) complex 2f have two additional methylene carbons.Cyclization of the alkyl groups attached to the silicon gave the spiro bicyclic Pt(II) complexes 10a and 11a and the Pt(IV) complexes 10 b and 11b.
Platinum complexes derived from b-silyamines
-
, (2008/06/13)
This invention relates to new cis diamino platinum complexes; to compositions comprising these complexes; and to processes for their utility as fungicides, bacteriocides and as inhibitors of the growth of cancer in warm-blooded animals, wherein the comple
AZOMETHINE YLIDE PRECURSORS: A SIMPLE ROUTE TO N-(TRIMETHYLSILYLMETHYL) IMINES
Letellier, M.,McPhee, D. J.,Griller, D.
, p. 1975 - 1978 (2007/10/02)
A simple synthesis of N-(trimethylsilylmethyl)amine is reported.This compounds was used to prepare N-(trimethylsilylmethyl)amines, useful sources of "nonstabilized" azomethine ylides.
Synthetic Versatility of N(Silylmethyl)imines: Water-Induced Generation of N-Protonated Azomethine Ylides of Nonstabilized Type and Fluoride-Induced Generation of 2-Azallyl Anions
Tsuge, Otohiko,Kanemasa, Shuji,Hatada, Akira,Matsuda, Koyo
, p. 2537 - 2546 (2007/10/02)
N-(Silylmethyl)imines generate N-protonated azomethine ylides of nonstabilized type when treated with water in HMPA, which undergo stereospecific and regioselective cycloadditions with electron-poor olefins affording N-unsubstituted pyrrolidines.On the other hand, fluoride-induced desilylation of the imines leads to 2-azallyl anions which are found to be synthetic equivalents of aminomethyl anion in the Michael additions with electron-poor olefins and nucleophilic additions with carbonyl compounds.
