65044-35-1Relevant academic research and scientific papers
Frustrated Lewis Pair Catalyzed Hydrogenation of Amides: Halides as Active Lewis Base in the Metal-Free Hydrogen Activation
Sitte, Nikolai A.,Bursch, Markus,Grimme, Stefan,Paradies, Jan
, p. 159 - 162 (2019/01/04)
A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,6-F2-C6H3)3 in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and α-branched carboxamides.
Conversion of Amides and Lactams to Thioamides and Thiolactams Using Hexamethyldisilathiane
Smith, D. C.,Lee, S. W.,Fuchs, P. L.
, p. 348 - 354 (2007/10/02)
Amides and lactams were converted to their corresponding thioamides and thiolactams employing a new protocol using hexamethyldisilathiane (TMS2S).Oxophilic promoters were employed to generate Vilsmeier-type intermediates, the most efficient reagents being phosphorus oxychloride, triphosgene, and oxalyl chloride.Thionation of intermediate chloro iminium ions was accomplished in situ with TMS2S.Yields were good to excellent for secondary and tertiary amides and lactams while yields for primary systems were poor.
Reactions of Relevance to the Chemistry of Aminoglycoside Antibiotics. Part 13. A Novel Synthesis of Benzyl Ethers
Barrett, Anthony G. M.,Read, Roger W.,Barton, Derek H. R.
, p. 2184 - 2190 (2007/10/02)
Benzyl ethers were prepared from alcohols by reaction with chloro(phenylmethyl)dimethylammonium chloride and sodium hydrogen telluride in sequence.The salt (1) 1)OR2Cl-; R1=H, R2=cholest-5-en-3β-yl> and sodium borohydride gave the borane complex of 3β-dimethylaminomethoxycholest-5-ene.Salt (1; R1=Ph, R2=cholest-5-en-3β-yl or 5α-cholestan-3β-yl) and ammonia or hydrazine gave the steroidal benzimidates or benzhydrazonate.
