Thiophen 2,5-diphenyl

If one considers that in the modifications, in place of the hydrocarbons, ethers, mono- and poly-add phenols, naphthalene, thiophene, diphenyl,naphthol-ethers, and many other compounds can be used, the great value of the Friedel-Crafts reaction will be readily understood. 

Benzo[6]thiophene, 2,3-dimethyltetrahydro-oxidative ring opening, 4, 768 Benzo[6]thiophene, 2,3-diphenyl-synthesis, 4, 109 Benzo[b]thiophene, 2-ethyl-synthesis, 4, 915 Benzo[6]thiophene, 2-fluoro-synthesis, 4, 932... 

Benzo[c]thiophene, 1,3-diphenyl-oxidative ring opening, 4, 768 synthesis, 4, 141-142... 

Ethylene, /3-(dimethylamino)-nitro-in pyrrole synthesis, 4, 334 Ethylene, dithienyl-in photochromic processes, 1, 387 Ethylene, furyl-2-nitro-dipole moments, 4, 555 Ethylene, l-(3-indolyl)-2-(pyridyl)-photocyclization, 4, 285 Ethylene, l-(2-methyl-3-indolyl)-l,2-diphenyl-synthesis, 4, 232 Ethylene, (phenylthio)-photocyclization thiophenes from, 4, 880 Ethylene carbonate C NMR, 6, 754 microwave spectroscopy, 6, 751 photochemical chlorination, 6, 769 synthesis, 6, 780 Ethylene oxide as pharmaceutical, 1, 157 thiophene synthesis from, 4, 899 Ethylene sulfate — see 2,2-dioxide under 1,3,2-Dioxathiolane... 

Naphtho[2,3-c]furan, 1,3-diphenyl-thiophene synthesis from, 4, 904 Naphthofurans aromaticity... 

Naphtho[2,3-h]thiophene, S-methyl-theoretical methods, 4, 3 Naphtho[2,3-c]thiophene, 1,3-diphenyl-synthesis, 4, 904... 

Thiophene, 3,5-diethyl-2,4-diphenyl-synthesis, 4, 900 Thiophene, dihydroconformation, 4, 34 cycloaddition reactions, 4, 850 H NM 4, 10 methiodide, 4, 86 molecular structure, 4, 7 1-oxide... 

Thiophene-2,4-dicarboxylic acid, 3,4-diphenyl-diethyl ester, 4, 135... 

The spectra and halochromism of thiophene analogs of triphenyl and diphenyl carbinol, " the spectra of anilides of 2- and 3-thenoyl-acetic acid, " and the fluorescence of some thiophene compounds have been investigated. 

The condensation of thiophene with ketones, under the influence of 70% H2SO4, leads to di-2-thienylmethane derivatives. With acetone, 2,2-di-(2-thienyl) propane (97) is obtained. The condensation of thiophene with dimethyl phenyl carbinol, methyl diphenyl carbinol, and f-butylalcohol, in the presence of SnCU gave (98), (99), and 2,5-di-f-butylthiophene, respectively. Triphenyl carbinol does not... 

Many stilbenelike thiophene compounds have been prepared for a study of estrogenic activity, especially by Buu-Hoi et al. Thiophene derivatives of nonhydroxylated stilbene types showed no significant activitywhereas weak estrogenic activity was found in 5-acetyl-, 5-propionyl-, and 5-benzoyl-2-(-stilbenyl)thiophene. 1-Bromo-l,2-diphenyl-2-(5-bromo-2-thienyl)ethylene (258) was found to inhibit body growth and to produce extensive testicular atropy in male rats. A thiophene analog of estrogenic isoflavones (259)... 

The 2-(2-pheriylvinyl) derivative 18 and the thienyl compound 20 cyclize exclusively at the alkene carbon, and at the thiophene ring, to give 3,4-diphenyl-l//-2-benzazepine (19) and 4-phenyl-6-//-thieno[3,2-e]-2-benzazepine (21), respectively.48 A mechanistic rationale for these results has been offered. This method has been extended to the synthesis of 7Z7-pyrido[3,4-t/]-, 7//-pyrido[2,3-t/]- and 77/-pyrido[4,3-r/]benzazepincs and to other thieno- and furo-fused 2-benzazepines.244... 

Natriumboranat/Kobalt(II)-chlorid (s.S. 115) reduziert aliphatische undaroma-tische Sulfoxide in Athanol mit guten Ausbeuten zu den entsprechenden Sulfanen. Mit dieser Methode erhalt man7 z.B. Dibutyl-sulfan (98% d.Th.), Diphenyl-sulfan (95% d. Th.) oder Thiuxanthen (100H/o d. Th.). Dibenzyl-sulfoxid und Tetrahydro-thiophen-1-oxid werden praktisch nicht angegriffen. 

Figure 33. UPS spectra of 2,5-bis(diphenyl-methylene)-2,5-dihydrothiophene, dihydro-selenophene and 2,5-bis(dithienylmethy-lene)-2,5-dihydrothiophene, as compared with those of benzene and thiophene.

Vigorous oxidation (CrOj/HOAc) of l,3,4,6-tetraphenyltiiieno[3,4-dthiophene (149) opens a ring, to yield 3,4-dibenzoyl-2,5-diphenyl-thiophene (60%). ... 

Sato and coworkers reported recently an interesting oxidation reaction of 1,4-dihydro-l,4-diphenyl-2,3-benzodithiin . When compound 38 was treated with m-CPBA in CH2CI2, ring contraction to l,3-diphenylbenzo[c]thiophene 39 was observed. With H2O2 in CH3COOH, the reaction afforded l,3-dihydro-l,3-diphenylbenzo[c]thiophene 40, while with Oxone a highly regioselective oxidized product, i.e. l,4-dihydro-l,4-diphenyl-2,3-benzodithiin 2,2-dioxide 41, was formed (equation 58). 

Photolysis of trans-2-phenyl-3-benzoylthietane yields both cis- and trans-l,3-diphenyl-2-ethenyl ketone and polymeric thioformaldehyde instead of the anticipated thiophene derivative. 

JOC2223>, as well as l,4-bis(/ rt-butylthio)-3,6-diphenyl- 185 and l,4-bis(/ r/-butylthio)-3,6-di-2-thie-nylthieno[3,4-c]thienophenes 186 <1998JOC163> were successfully synthesized as isolable compounds. These isolable thieno [3,4-f]thiophenes owe their stability to steric hindrance together with resonance and the electron-withdrawing effects of the substituents. 

The protonation of 185 and 186 with trifluoroacetic acid (TFA) gave 4-(/i t/-butylthio)-3,6-diphenyl- 193 and 4-(ter1-butylthio)-3,6-di(2-thienyl)thieno[3,4-f]thiophene-l(3//)-thione 194 (Scheme 18). The treatment of 193 with sodium hydride and then isopropyl iodide led to 4-(/i< t/-butylthio)-3,6-diphenyl-l-(isopropylthio)thieno[3,4-f]thio-phene 195 by the regeneration of the thieno[3,4-f]thiophene ring system, thus making possible the synthesis of other alkylthio-substituted thieno[3,4-(r]thiophene derivatives. When the reaction of 185 with TFA was carried out... 

Unter Amin-Katalyse setzt sich 4-Acetoxy-2,5-diphenyl-3-hydroxy-thiophen-l,l-dioxid als aktivierter Ester in siedendem Toluol in guter Ausbeute mit Carbonsaure-amid-hydrox-imiden zu 1,2,4-Oxadiazolen urn 1 z.B. ... 

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