90606-07-8Relevant academic research and scientific papers
Silyl-Substituted Thioimidates as Nitrile Ylide Equivalents
Padwa, Albert,Gasdaska, John R.,Haffmanns, Gunter,Rebello, Hector
, p. 1027 - 1035 (2007/10/02)
Treatment of silyl-substituted thioimidates with silver fluoride in the presence of a trapping agent produces dipolar cycloadducts formally derived from nitrile ylides.The ratio of cycloadducts obtained from the reaction of unsymmetrically substituted dip
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.
One-Pot Synthesis of N-((Trimethylsilyl)methyl)imines and (Trimethylsilyl)methyl-Substituted Heterocumulenes from (Trimethylsilyl)methyl Azide
Tsuge, Otohiko,Kanemasa, Shuji,Matsuda, Koyo
, p. 2688 - 2691 (2007/10/02)
The reactions of ((trimethylsilyl)methyl)iminotriphenylphosphorane, prepared in situ from (trimethylsilyl)methyl azide and triphenylphosphine, with carbonyl compounds and with heterocumulenes such as carbon dioxide, carbon disulfide, isocyanates, isothiocyanates, and a ketene provide convenient one-pot syntheses of the corresponding N-((trimethylsilyl)methyl)imines and (trimethylsilyl)methyl-substituted heterocumulenes, which are versatile reagents for the synthesis of heterocyclic compounds.
