2-cyclohexyl-4,5-diphenyl

Information concerning the chemistry of meso-ionic 3-alkyl- and 3-aryl-l,2,3,4-oxatriazol-5-ones (271) is limited, but further investigation may well be encouraged by reports of pronounced hypotensive activity. 3-Cyclohexyl-1,2,3,4-oxatriazol-5-one (271, R = cyclohexyl) is resistant to attack by dilute mineral acid, but warm concentrated sulfuric acid gives cyclohexanol and carbon dioxide. In contrast, acid hydrolysis of 3-phenyl-l,2,3,4-oxatriazol-5-one (271, R = Ph) yields phenyl azide. Meso-ionic 3-cyclohexyl-l,2,3,4-oxatriazol-5-one shows two unusual reactions its photoirradiation in benzene gives cyclohexanone and heating with diphenylacetylene )delds l-cyclohexyl-4,5-diphenyl-1,2,3-triazole (276) rather than the expected 2-cyclohexyl-4,5-diphenyl-1,2,3-triazole. 

CfiHj, o 0 (H,C.)21LQ I-Cydohexenyl-1 diphenyt-phosphan-oxid 28 121-122 0,05 (6,5 10% o Cl ih5c6i2p- 0 u 0H ih5c6)2p- ] ( 7 - Chlor-cyclohexyl) diphenyl-+ Diphenyl- (l-hydroxy-cyclohexyl)-phosphanoxid 90... 

R = C6Hu Cyclohexyl-diphenyl-phosphanoxid 57% R = C8H17 Diphenyl-octyl-phosphanoxid 50%... 

CaoHuO Cyclohexyl-diphenyl-carbinol-methyh ther 6 II 668. 

C2 8H2 8AS3CoCr2FeOi2 r Tricarbonyl-(dicarbonyl(tricarbonyl(cyclopenta-dienyl)chromium)cyclopentadienyl-/Li"(dimethylarsenido)chromium)-bis-M (dimethylarsenido)-(tetracarbonyliron)cobalt, 46B, 905 C28H2eCoNi04P, Di-/x"carbony1-dicarbony1(cyclohexyl(diphenyl)phosphine) (TT-methylcyclopentadienylnickelio)cobalt, 4IB, 910 C2 eH28N2S2Ti2, (2,4-Dithiopyrimidinato)bis[bis(T -methylcyclopenta-dienyl)titanium(III)], 45B, 981... 

Abbreviations acac, acetylacetonate Aik, alkyl AN, acetonitrile bpy, 2,2 -bipyridine Bu, butyl cod, 1,5- or 1,4-cyclooctadiene coe, cyclooctene cot, cyclooctatetraene Cp, cyclopentadienyl Cp, pentamethylcyclopenladienyl Cy, cyclohexyl dme, 1,2-dimethoxyethane dpe, bis(diphenyl-phosphino)ethane dppen, cis-l,2-bis(di[Atenylphosphino)ethylene dppm, bis(diphenylphosphino) methane dppp, l,3-bis(diphenylphosphino)propane eda,ethylenediamine Et,ethyl Hal,halide Hpz, pyrazole HPz, variously substituted pyrazoles Hpz, 3,5-dimethylpyrazole Me, methyl Mes, mesityl nbd, notboma-2,5-diene OBor, (lS)-endo-(-)-bomoxy Ph, phenyl phen, LlO-phenanthroline Pr, f opyl py, pyridine pz, pyrazolate Pz, variously substituted pyrazolates pz, 3,5-dimethylpyrazolate solv, solvent tfb, tetrafluorobenzo(5,6]bicyclo(2.2.2]octa-2,5,7-triene (tetrafluorobenzobanelene) THE, tetrahydrofuran tht, tetrahydrothicphene Tol, tolyl. 

Prenyl amine (66) was long used in the treatment of angina pectoris, in which condition it was believed to act by inhibiting the uptake and storage of catecholamines in heart tissue. Droprenilamine (69), an analogue in which the phenyl ring is reduced, acts as a coronary vasodilator. One of several syntheses involves simple reductive alkylation of 1,1-diphenyl-propylamine (67) with cyclohexyl acetone (68)... 

Cyclohexyl-2,5-diphenyl-3,4,7-triazanorcara-2,4-dienc gives 4-cyclohexyl-3,7-diphenyl-4//-1,2.4-triazepine (59%) together with A-cyclohexyl-3,6-diphenylpyridazin-4-amine and 1-cyc-lohexyl-2.3-diphenylpyrrole. No further details were reported. 

Phosphine, (2-bromophenyl)dichloro-, 2,991 Phosphine, (w-chloroalkyl)dichloro-, 2, 991 Phosphine, chlorodimethyl-, 2, 991 Phosphine, chloro(dimethylamino)-, 2, 991 Phosphine, chlorodiphenyl-, 2, 990 Phosphine, cyclohexyl(o-anisyl)methyl-rhodium complexes asymmetric hydrogenation, 6, 251 Phosphine, [(dialkylphosphino)alkyl]diphenyl-, 2, 994 Phosphine, dichloromethyl-, 2, 991 Phosphine, dichlorophenyl-, 2, 990 Phosphine, diethylphenyl-, 2, 992 Phosphine, dimethyl-, 2,992 Phosphine, dimethylphenyl-, 2,992 Phosphine, diphenyl-, 2, 992 Phosphine, ethyldiphenyl-, 2, 992 Phosphine, ethylenebis(diethyl-, 2, 993 Phosphine, ethylenebis(diphenyl-, 2,993 Phosphine, ethylenebis(phenyl-, 2,992 Phosphine, ethylidynetris[methylene(diphenyl-, 2,994 Phosphine, [(ethylphenylphosphino)hexyl]diphenyl-, 2, 994... 

Isocyanide, benzyl, 55, 98 Isocyanide, butyl-, 55, 98 Isocyanide, cyclohexyl-, 55, 98 ISOCYANIDE, 1,1-dimethylethyl- [Isocy-amde, tert-butyl-], 55,96 Isocyanide, dodecanyl- 55,98 Isocyanide, ethyl- 55,98 Isocyanide, methyl-, 55, 98 Isocyanide, phenyl-, 55, 98 1//Isoindole 1,3(2//) dione, 2 amino [Phthahmidc, N-amino-], 55, 115 1//-ISOINDOLE-1,3(2//)-DIONE, trans-( )-2-(2,3-diphenyl-l-aziridinvl)-[Azindine, frans-2,3-diphenyl-l-phthalimido-], 55, 115 ISOXAZOLE, 3-(4-chlorophenyl)-5-(4-methoxy phenyl)-, 55, 39 Isoxazole 5-(4-chlorophenyl)-3-(4-meth-oxyphenyl)-, 55, 42... 

N-Diphenylmethylen- 374 N-Diphenylmethylen-O-aminocarbonyl- 612 N-[l,3-Diphenyl-propyl-(2) - 374 N-[l,3-Diphenyl-propyliden-(2)]- 374, 377, 380 N-(4-Halogen-phenyI)- 683 N-Heptyl- 375 N-Heptyl-N-acetyl- 376 N-Heptyliden- 375 N-Hcptyliden-O-acetyl- 376 0-(2-Hydroxy-athyl)-N-athoxycarbonyl- 133 N-(4-Hydroxy-phenyl)- 683 0-(2-Hydroxy-l-phenyl-athyI)-N-athoxycarbonyI-aus 0-(ci-AthoxycarbonyI-benzyl)-N-athoxycar-bonyl-hydroxylamin und Lithiumalanat 133 N-Isopropyl- 682 N-Isopropylidcn- 613 N-Methyl- 133, 682 O-Methyl-N-bcnzyliden- 377 O-Methyl-N-benzyliden- 375 0-Methyl-N-(4-chlor-benzyl)- 375 0-Methyl-N-(4-chlor-benzyliden)- 375 N-Methy -N,0-diacetyI- 682 N-(4-Methyl-phenyl)- 683 0-McthyI-N-( 1 -phenyl-athyliden)- 375 N-(4-Methylthio-phenyl)- 684 N-(4-Nitro-benzyl)- 374 N-[4-Nitro-benzyliden - 374, 377 N-(2-Nitro-phenyl)- 562 N-(4-Nitro-phenyl)- 682 N-Nitroso-N-cyclohexyl- 697 N-Octyl- 374 N-Octyl-(2)-N-acetyl- 376 N-Octyliden- 374 N-0ctyliden-(2)-0-acctyl- 376 N-(Pentafluor-phenyl)-0,N-diacetyl- 697 N-Phenyl- 474, 481, 682, 783 N-Phenylacetyl-O-benzoyl- 265 N-(l-Phenyl-athyl)- 374 N-(l-Phenyl-athyl)-N-acetyl- 376 N-(l-Phenyl-athyliden)-374, 613 N-( l-Phenyl-athyliden)-0-acetyl- 376 N-[ 1 -Phenyl-buten-( 1 )-yl-(3)-iden]- 582 N-f4-Phenyl-butyl-(2)-iden]- 581 N-Phcnyl-N,0-diacetyl- 682 N-(4-Phenylthio-phenyl)- 684 N-Propyl-N-cyclohexyl- 376 N-Propyl-N-isopropyl- 376 O-Sulfonyl- 481 N-(4-Sulfonyl-phenyI)- 683 N-(2-Vinyl-phenyl)- 698... 

Brom-bis- 4-brom-2-oxo-l,3-dioxolan-5-yl]- 527 Brom-bis-[butyIsuIfonyI]- 621 Brom-bis-[methyIsulfonyl]- 621 Brom-cyclohexyl- 392 Brom-diphenyl- 505. 668... 

Cyclohexyl-( 1 -hydroxy-cyclohexyl)- 609 Diphenyl- -athylester 637 Diphenyl- -butylester 637 f. 

Production of considerable amounts of cyclohexanol and cyclohexanone as well as benzaldehyde and benzoic acid in the oxidation of benzyl cyclohexyl ether shows the primary radical to be CgHjCHOCeHjj. Abstraction from aliphatic C-H bonds cannot occur in the case of diphenyl ether which is oxidised rapidly, and removal of a 7t-electron is likely. 

The conversion of symmetrical into unsymmetrical thioureas is exemplified by the formation of Af-cyclohexyl-Af -phenylthiourea when yV,iV-diphenyl thiourea is heated with cyclohexylamine and triethylamine in acetonitrile367. Carbonylation of lithium piperidide in the presence of tellurium generates the lithium carbamotellurate 307, which is trapped as the 7V-ethyl carbamotellurate 308 by ethyl bromide368. 

Several 1,4-disubstituted derivatives of the dication, 63, were successfully prepared. The 1,4-diphenyl, 1,4-dimethyl, 1,4-dicyclopropyl-substituted derivatives of carbodication 63 (65, 66, and 67) are exceptionally stable. The 1,4-dimethyl-1,4-cyclohexyl dication, devoid of the adjacent cyclopropyl groups, could not be prepared. The carbocationic center in all these dications are somewhat shielded as compared to their monocations. The C NMR chemical shifts of the carbocationic centers for the dications 65, 66, and 67 are 235.4, 293.4, and 260.8 ppm, respectively. The diprotonated ann -tricyclo(5.1.0.0 )octa-2,6-dione, 68, may be treated as a dicarboxonium ion, instead of dihydroxy dicarbenium ion, since the cabronyl carbon is shielded by only 25.2 ppm, much smaller than that observed for the protonated cyclohexanedione (34 ppm). The para carbons of the phenyl substituents in carbodication 65 are relatively shielded by about 5 ppm from that of the parent l,4-diphenylcyclohexane-l,4-diyl dication showing relatively less delocalization of the charge into the aromatic rings. 

Problem 14.55 Prepare the following ethers starting with benzene, toluene, phenol (C H OH), cyclohexanol, any aliphatic compound of three C s or less and any solvent or inorganic reagent a) dibenzyl ether, b) di-/i-butyl ether, (c) ethyl isopropyl ether, d) cyclohexyl methyl ether, (e) p-nitrophenyl ethyl ether, (/) divinyl ether (g) diphenyl ether. <... 

Hydrophobic sorbents including octadecyl, octyl, diphenyl, cyclohexyl, phenyl, butyl, ethyl, methyl, and copolymers of styrene and divinylbenzene can be applied for retaining nonpolar to medium polar analytes. In this list, the styr-ene-divinylbenzene copolymer phases such as PRP-1 and XAD-2 are the most nonpolar phases, while the methyl phase is the least nonpolar one. The analytes are adsorbed onto the hydrophobic materials by means of van der Waals interactions and, to some extent, by hydrophobic bonding or dipole-dipole interactions. 

---