Phenethyl carbamate

Phenethyl carbamate derivatives 30 have also been employed in Bischler-Napieralski reactions cyclization of these substrates affords 3,4-dihydroisoquinolones 31. These reactions have been conducted using a variety of different promoters including PPA, POCl3, and Tf20. Mixtures of P2O5 and POCI3 appear to afford the best results in some cases. 

The Daicel polysaccharide CSPs that became available in 1985 have been largely used in the field of atropisomeric heterocycles both at the analytical or semipreparative scale. Cellulose tris (p-methylbenzoate), cellulose tris(3,5-dimethylphenylcarbamate), amylose tris(3,5-dimethylphe-nyl-carbamate), and amylose tris[(S)alpha-phenethyl]carbamate) were... 

Different iV-methylation derivatives of moloka iamine, aplysamine 1 (54) 44), purealidin F (55), and G (56) 45), were obtained from an Australian sponge Aplysina sp. and the Okinawan sponge Pscanmaplysilla purea, respectively. 3,5-Dibromo-4-(3-dimethylaminopropoxy)phenethyl carbamic acid methyl ester (57) and its salt 58 were obtained as the first bromotyrosine derivatives containing a carbamate group from an Indian sample of Psammaplysilla purpurea 46), along with 59 47,48). 

Substitution on the phenethyl side chain of the substrate is usually well tolerated. For example, reaction of carbamate 44 with POCI3 afforded a 75% yield of the corresponding lactam 45. However, in some instances substituents on the chain lead to low yields, such as in the reaction of amide 46, which provided only a 29% yield of the desired product 47 (albeit with 9 1 diastereoselectivity). ... 

The nickel(II) dithiocarbamate complexes are neutral, water-insoluble, usually square-planar, species, and they have been studied extensively by a range of physical techniques. The usual methods for the synthesis of dithiocarbamate complexes have been employed in the case of Ni(II), Pd(II), and Pt(II). In addition, McCormick and co-workers (330,332) found that CS2 inserted into the Ni-N bonds of [Ni(aziri-dine)4P+, [Nilaziridinelgf, and [Ni(2-methylaziridine)4] to afford dithiocarbamate complexes. The diamagnetic products are probably planar, but they have properties typical of dithiocarbamate complexes, and IR- and electronic-spectral measurements suggested that they may be examples of N,S-, rather than S,S-, bonded dithiocarbamates. The S,S-bonded complexes are however, obtained, by a slow rearrangement in methanol. The optically active lV-alkyl-iV(a-phenethyl)dithio-carbamates of Ni(II), Pd(II), and Cu(II) (XXIV) have been synthesized, and the optical activity was found to be related to the anisotropy of the charge-transfer transitions (332). 

Me and coworkers reported a novel oxidation reaction of Af-Boc-phenethyl amines 21a and 21b to the corresponding cyclic carbamate 22 and aldehydes 23a and 23b (equation 21). ... 

Table 17), but cyclization of -substituted carbamates is highly selective (entries 2,4 and 5), presumably by insuring reversible formation of the intermediate prior to benzyl cleavage and steric interactions between the -substituent and the alkyl substituent favoring the axial orientation (equation 61). Cycliza-tions of this type, where R = H and Y = a-phenethyl, result in little asymmetric induction. However, the diastereomeric products can be separated and used for the synthesis of chiral nonracemic amino alcohol derivatives.164... 

Stalcup, A. M. Comparison ofthe enantioselectivity of phenethyl- and naphthyl-ethyl-carbamate substituted cyclodextrin bonded phases,/. Liq. Chromatogr., 1993,... 

Hydroxyphenamate. 2-Phenyl-l,2-butanediol 1-carbamate carbamic acid ft -ethyl -0-hydroxy phenethy] ester d-ethyl-p-hydroxyphenethy] carbamic acid ester 0-ethyl-0-hydroxy phenethyl carbemate 2-hydroxy-2-phenyl-butyl carbamate Al 0361 Listica. C.,H.sNOv mol wt 209.24. C 63.14%, H 7.23%, N 6.69%, O 22 94%. Prepd from d-ethyl -d-hydroxyphenethyl alcohol and ethyl chloro-formate followed by reaction with ammonia Sifferd, Brait-berg. U,S. pat. 3,066,164 (1962 to Armour-Pharm.). Pharmacology and toxicology Bastian, Clements, Di-V. Nerv. Sys. 22, 9 (1961). 

The advantage of a fluoride leaving group was clear in reaction of a hydroxy-carbamate anion with (fluorobenzene)FeCp complex, where the yield was 72% for F and 41% for Cl [79]. The (l,2-difluorobenzene)FeCp complex underwent smooth double substitution with phenethyl amine, whereas a dichloro complex led to monosubstitution. Replacement of a nitro group in q -nitrobenzene-FeCp" is possible with O, S, and N-nucleophiles [70,80,81]. The nitroarene complexes, which are not known in the Cr(CO)3 series, are prepared by oxidation of the corresponding aniline complexes. 

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