4- Phenyl-3-phenylsulfonyl- 723

Initially, the allylation reaction was studied with the /V-benzyloxycarbonylamino sulfone derived from benzaldehyde and benzoyloxycarbonyl (Cbz) carbamate (Scheme 1, R1 = Ph, R = Bn). Various catalysts were screened for the allylation of benzyl phenyl(phenylsulfonyl)methylcarbamate la with allyltrimethylsilane in dichloromethane (Table 1). Among the various Bi catalysts tested, Bi(OTf)3 4H20 was shown to be the most efficient (Table 1, entry 5). BiCl3, BiBr3, Bi(OAc)3, or Bi(OCOCF3)3 did not allow the reaction to proceed and starting material was... 

Conditions benzyl phenyl(phenylsulfonyl)methylcarbamate la (1.0 equiv.), allyltrimethylsilane (1.5 equiv.), metal salt (2 mol%) in dry CH2C12 at 22 °C for 5 h Isolated yield... 

Phenyl phenylsulfonyl sulfate 0=S(0)(Ph)(PhS02) 122 510.4 Derived 1978BEN... 

A soln. of startg. chlorosulfone in DMF added via syringe to a stirred soln. of KOBu-/ in the same solvent at —40° under argon, after 5 min tropylium fluoroborate in DMF added dropwise during ca. 5 min below —40°, and stirred for a further 5 min - chloro(7-cycloheptatrienyl)phenyl(phenylsulfonyl)methane. Y 65%. F.e. and hepta-fulvenes by 1,2-elimination s. S. Ostrowski, M. Makosza, Ann. Chem. 1989, 95-7. 

Matrix investigations of sulfur and phosphorus analogues of acarbonylcarbenes have also been reported. For example, diphenylsulfene (66) and diphenyl-a-sultine (67) were isolated in low-temperature matrices following the thermal reaction of SO2 and diphenylcarbene (65) and the stepwise photolysis of phenyl(phenylsulfonyl)diazomethane (68), as summarized in Scheme 8. The ultimate photoproduct was benzophenone (70). 

Ethyl-4-methyl-l-(phenylsulfonyl)indole 4-Ethyl-7-methyl-l-phenylsulfonyl-l,5-dihydropyrano-[3,4-b]pyrrol-5-one phenyl vinyl sulfoxide 60 [3]... 

X-ray, 4, 160 (79AX(B)2228> lH-Pyrrole-2,4-diamine, 1-t-butyl-JV, JV -dimethyl-3-phenyl-JV -phenylsulfonyl-X-ray, 4, 160 (78BSB893) lH-Pyrrole-3-methanol, 4-acetyl-X-ray, 4, 160 (78AX(B)1248> lH-Pyrrole-3-methanol, 4-acetyl-, hydrate X-ray, 4, 160 (78AX(B)1248> lH-Pyrrole-3-propanoic acid, ester C NMR, 4, 172 (74JCS(P2)1004>... 

The reaction of 3-methoxy-1,2,4-triazine 1-oxide 20 with the carbanion generated from chloromethyl phenyl sulfone proceeds as the vicarious nucleophilic substitution (VNS) of hydrogen (Scheme 1, path B) via addition of the carbanion at position 5 of the heterocycle. Following base-induced elimination of HCl and protonation, 3-methoxy-5-phenylsulfonyl-1,2,4-triazine 4-oxides 65 result (88LA627). 

Dicyano-2,4,8-triphenyl-7-phenylsulfonyl-6/f-pyrido[], 2-a]pyrimi-dine-6-thione was obtained in the reaction of 6-amino-1-benzoyl-5-cyano-4-phenyl-3-phenylsulfonylpyridin-2(]//)-one and benzylidenemalononitrile in the presence of piperidine in boiling dioxane for 4h in 59% yields (98M1049). 

Finke, P. E., Oates, B., Mills, S. G., MacCoss, M., Malkowitz, L., Springer, M. S., Gould, S. L., DeMartino, J. A., Carella, A. Carver, G., et al. (2001). Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 4 synthesis and structure—Activity relationships for l-[7V-(Methyl)-7V-(phenylsulfonyl)amino]-2-(phenyl)-4-(4-(7V-(alkyl)-7V-(benzylox-ycarbonyl)amino)piperidin-l-yl)butanes. Bioorg. Med. Chem. Lett. 11 2475-2479. 

The addition of methyllithium to -alkoxy-a-(trimethylsilyl)-of/ unsaturated sulfones, 3-alkoxy-5-phenyl-l-phenylsulfonyl-l-(trimethylsilyl)-l-pentene and subsequent desilylation gives syn-products. The syn to anti diastereoselectivity is generally high and essentially independent of the nature of the y-alkoxy substituent8-13. 

A novel application of a phenyl aryldiazosulfone was found by Kessler et al. (1990). l-[4-(7V-Chlorocarbonyl-7V-methylamino)phenyl]-2-(phenylsulfonyl)diazene (6.18) is an acid chloride with a potential diazonio group. The above authors showed that in organic solvents (THF, etc.) this compound reacts easily, as expected, with nucleophiles (HNu), e.g., with aliphatic, aromatic, or heterocyclic amines, with cystine dimethyl ester, or with 4-methoxyphenol at the carbonyl function, yielding... 

Ohne Protonendonator wird l-Phenyl-2-phenylsulfonyl-propanol unter Dimerisierung und C—C-Spaltung reduziert2 ... 

Phenyl- 50, 55, 398, 514, 522, 581, 633, 645ff. 2-Phenyl-l-(2-hydroxylamino-phenyl)- 698 2-Phenyl-1 -(2-nitro-phenyl)- 698 2-Phenyl-1 -(2-nitroso-phenyl)- 698 2-Phenyl- -sulfinsaure 461 2-Phenyl- -sulfonsSure-chlorid 461 2-Phenylsulfonyl-1,1 -diphenyl- 634 Phenylsulfonyl-triphenyl- 464 Tetraaryl-... 

Phenylsulfonyl-2-oxo-l-(4-methoxy-phenyl)- 633 3-Phenylsulfonyl-2-oxo-1 -phenyl- 633 2-Phenylthio-2-methyl- 500 2-Piperidino-l-(4-methyl-phenylthio)- 500... 

Phenyl vinyl sulfones reacted with cyclohexanone enamines 332 to afford adducts which, upon hydrolysis, gave 2-(2-phenylsulfonyl)alkylcyclohexanone 333a . However, in the reaction with phenyl styryl sulfone, two products 333b and 334 were obtained by the nucleophilic attack at the and a-carbon atoms . Steric effects, electrostatic interactions between the nitrogen atom of the enamine and the oxygen atoms of the sulfone group, and medium effects contribute to the regioselectivity of the reaction. ... 

Synthetic Method 9 N-[8-bis(2-cyanoethyI) -9-[4- (phenylsulfonyl) -benzoyl]-9, 10-dihydro-1 0-phenyl-2-phenazinyl]-4-phenylsulfonylbenzamide (53) (procedure from US. Patent 4,889,932).18 A 3-liter round-bottom flask fitted with a mechanical stirrer was loaded with 16.6 g (0.066 mol) of 4-[di(2-cyanoethyl)amino]aniline in 800 ml of deionized water. A 10% excess of aniline (13.56 g, 0.1456 mol) and 100ml of deionized water were added to the mixture. The mixture was cooled to 0°C in an ice bath, and... 

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