73885-72-0Relevant academic research and scientific papers
Various oxidative reactions with novel ion-supported (diacetoxyiodo) benzenes
Iinuma, Masataka,Moriyama, Katsuhiko,Togo, Hideo
, p. 2961 - 2970 (2013/04/10)
The oxidation of secondary alcohols and primary alcohols with two novel ion-supported (diacetoxyiodo)benzenes (IS-DIBs) A and B in the presence of a catalytic amount of 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO) in dichloromethane at room temperature proceeded efficiently to provide the corresponding ketones and aldehydes, respectively, in good yields. The oxidative reaction of N,N-diisopropylbenzylamines with those IS-DIBs was also carried out to generate the corresponding aromatic aldehydes in good yields. In addition, the Hofmann rearrangement of primary amides in methanol under basic conditions and the oxidative 1,2-rearrangement of propiophenones in trimethyl orthoformate under acidic conditions with those IS-DIBs provided the corresponding methyl carbamates and methyl 2-arylpropanoates, respectively, in good yields. Moreover, treatment of acetophenones with those IS-DIBs in the presence of trifluoromethanesulfonic acid in acetonitrile generated the corresponding 5-aryl-2-methyloxazoles in good yields. In those five reactions, the desired products were obtained in good yields with high purity by simple extraction of the reaction mixture with diethyl ether and subsequent removal of the solvent from the extract. Moreover, ion-supported iodobenzenes, which were the co-products derived from IS-DIBs in the present oxidative reactions, were recovered in good yields and could be re-oxidized to IS-DIBs A and B for reuse in the same oxidative reactions.
A convenient method for synthesis of optically active β-hydroxyamines from primary amines through enecarbamates as key intermediates
Matsumura, Yoshihiro,Ohishi, Takahiro,Sonoda, Chihiro,Maki, Toshihide,Watanabe, Mitsuaki
, p. 4579 - 4592 (2007/10/03)
This report describes a new method to prepare optically active β-hydroxamines starting from primary amines. The method consists of a transformation of N-methoxycarbonylated primary amines to the corresponding enecarbamates utilizing electrochemical oxidat
Preparation of Methyl Carbamates from Primary Alkyl- and Arylcarboxamides Using Hypervalent Iodine
Moriarty, Robert M.,Chany, Calvin J.,Vaid, Rahde K.,Prakash, Om,Tuladhar, Sudersan M.
, p. 2478 - 2482 (2007/10/02)
A series of 14 primary alkyl- and arylcarboxamides were treated with PhI(OAc)2 in KOH-CH3OH at 5-10 deg C to give the corresponding methyl carbamates in good to excellent yields.These conditions avoid the use of elemental bromine or heavy metal reagents (Pb(OAc)4, AgOAc, Hg(OAc)2), while taking advantage of the commercial availability of PhI(OAc)2.The methyl carbamates are easily purified via column chromatography on silica gel.The isolated yields of the carbamates ranged from 72percent for methyl N-cyclopropylcarbamate to 97percent for methyl N-phenylcarbamate.
A facile approach to arylacetaldehydes via polymeric palladium catalyst
Zhuangyu,Yi,Honwen,Tsi-yu
, p. 539 - 542 (2007/10/02)
Several arylacetaldehydes 5 were synthesized in moderate yields via Heck reaction of acrylamide (1) with substituted iodobenzenes 2 in the presence of the polymeric catalyst (P)-phenyl-(1,10-phenanthroline)-palladium(0) [(P)-ph-phen·Pd(0)] followed by Hofmann reaction and subsequent hydrolysis.
Synthesis of Enamides
Brettle, Roger,Mosedale, Alan J.
, p. 2185 - 2196 (2007/10/02)
(Z)-3-Arylprop-2-enoic acids can be converted by the Curtius procedure, through the acyl azides, into (Z)-2-arylethenyl isocyanates, which with methanol give methyl (Z)-N-(2-arylethenyl)carbamates.Acylation of the (Z)-enecarbamates, through their anions, leads to methyl (Z)-N-acyl-N-(2-arylethenyl)carbamates, which on treatment with lithium iodide in boiling N,N-dimethylformamide or acetonitrile undergo demethoxycarbonylation to give (Z)-enamides.The stereospecific route to enamides can also be used in the E-series.Treatment of (Z)- or (E)-2-arylethenyl isocyanates with trifluoroacetic acid gives (E)-N-(2-arylethenyl)trifluoroacetamides,the anions of which, with acylating agents, give (E)-enamides directly.
