5338-49-8Relevant academic research and scientific papers
Smooth isoindolinone formation from isopropyl carbamates via bischler-napieralski-type cyclization
Adachi, Satoshi,Onozuka, Masao,Yoshida, Yuko,Ide, Mitsuaki,Saikawa, Yoko,Nakata, Masaya
supporting information, p. 358 - 361 (2014/04/03)
Isopropyl carbamates derived from benzylamines provide isoindolinones by treatment with phosphorus pentoxide at room temperature. Utility of this Bischler-Napieralski-type cyclization and a new mechanism involving a carbamoyl cation for rationalization of this smooth conversion are discussed.
Heterogeneous CeO2 catalyst for the one-pot synthesis of organic carbamates from amines, CO2 and alcohols
Honda, Masayoshi,Sonehara, Satoru,Yasuda, Hiroshi,Nakagawa, Yoshinao,Tomishige, Keiichi
scheme or table, p. 3406 - 3413 (2012/01/15)
Heterogeneous CeO2 catalyst can catalyze the one-pot synthesis of methyl benzylcarbamate from benzylamine, CO2 and methanol. The yield of methyl benzylcarbamate reached 92% at >99% benzylamine conversion and 92% benzylamine-based selectivity even in the absence of the dehydrating agents. The catalyst is reusable after the calcination at 873 K for 3 h. Various carbamates can be synthesized with good yield and high selectivity by the reaction of amines + CO2 + alcohols over CeO2. The main formation route of methyl benzylcarbamate is suggested to be the reaction of dimethyl carbonate or the precursor of dimethyl carbonate formation with benzylamine.
Effect of successive increase in alcohol chains on reaction with isocyanates and isothiocyanates
Perveen, Shahnaz,Yasmin, Arfa,Khan, Khalid Mohammed
experimental part, p. 18 - 23 (2010/04/23)
The reaction of isocyanates and isothiocyanates with long-chain alcohols, e.g. n-hexanol, n-heptanol and n-octanol, exclusively gave N-aryl-O-alkyl carbamates, while N-aryl-O-alkyl carbamates were formed along with symmetrical 1,3-disubstituted ureas and thioureas when the same reactions were carried out with small-chain alcohols at room temperature without using any solvent.
Pd-catalyzed N-arylation of secondary acyclic amides: Catalyst development, scope, and computational study
Hicks, Jacqueline D.,Hyde, Alan M.,Cuezva, Alberto Martinez,Buchwald, Stephen L.
supporting information; experimental part, p. 16720 - 16734 (2010/04/04)
We report the efficient N-arylation of acyclic secondary amides and related nucleophiles with aryl nonaflates, triflates, and chlorides. This method allows for easy variation of the aromatic component in tertiary aryl amides. A new biaryl phosphine with P-bound 3,5-(bis)trifluoromethylphenyl groups was found to be uniquely effective for this amidation. The critical aspects of the ligand were explored through synthetic, mechanistic, and computational studies. Systematic variation of the ligand revealed the importance of (1) a methoxy group on the aromatic carbon of the "top ring" ortho to the phosphorus and (2) two highly electron-withdrawing P-bound 3,5-(bis)trifluoromethylphenyl groups. Computational studies suggest the electron-deficient nature of the ligand is important in facilitating amide binding to the LPd(II)(Ph)(X) intermediate.
Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers
Kim, Ji Duck,Han, Gyoonhee,Jeong, Lak Shin,Park, Hyun-Ju,Zee, Ok Pyo,Jung, Young Hoon
, p. 4395 - 4402 (2007/10/03)
The stability order of various alkyl, allyl, and benzyl carbocations was investigated using the novel technique for comparing the stability of carbocations in solution developed by using a simple CSI reaction with various ethers. The p-methoxycinnamyl carbocation was the most stable in our reaction system and the next stable carbocation was the p-methoxybenzyl carbocation. The stability of the other carbocations decreased with methacryl, t-butyl, cinnamyl, acryl, benzyl, 2° and allyl carbocations in that order.
α-Haloalkyl Haloformates and Related Compounds 1. A Convenient Synthesis of Carbamates via Chloromethyl Carbamates
Patonay, Tamas,Patonay-Peli, Erzsebet,Mogyorodi, Ferenc
, p. 2865 - 2885 (2007/10/02)
The preparation of carbamates under mild conditions utilizing a new class of activated carbonates (containing chloromethyl function) is described.
New Agents for Alkoxycarbonylation of Amines
Ohta, Akihiro,Inagawa, Yukiko,Inoue, Masami,Shimazaki, Makoto,Mamiya, Yukari
, p. 1173 - 1177 (2007/10/02)
Alkoxycarbonylated pyrazinols and pyrazinethiols were prepared.These compounds were shown to be convenient agents for alkoxycarbonylation of aliphatic amines.
Reactions of Primary and Secondary Amines with Fluoronitrene Generated from Isopropyl N,N-Difluorocarbamate
Klopotek, David L.,Hobrock, Brice G.,Kovacic, Peter,Jones, Martin B.
, p. 1665 - 1667 (2007/10/02)
Isopropyl N,N-difluorocarbamate deaminates primary amines, RNH2, affording RH, N2, RNHCO2-i-C3H7, and RNH2*HF.With secondary amines, dibenzylamine gives bibenzyl, whereas pyrrolidine yields a ring-expansion product, 2,3,4,5-tetrahydropyridazine.The reactions are consistent with the generation of fluoronitrene and subsequent production of the intermediates RN=NH from RNH2 and R2N=N from R2NH.The advantages of using isopropyl N,N-difluorocarbamate as a source of fluoronitrene are discussed.
