2 ’- ethyl benzenethiol

Copper aienethiolate 1-Cu can be prepared starting from (/ )-2-[l-(dimethylamino)ethyl]benzenethiol and CU2O, ot from the corresponding trimethylsilyl thio ether and CuCl (eq 5). ... 

The method outlined here competes well with the method developed earlier by Danheiser, et al.618 Its superiority is based on the fact that phenyl ester enolates give almost the same results as the S-phenyl thiolester enolates. However, handling the malodorous benzenethiol for the preparation of the active acid derivative and during workup of the p-lactone can be avoided. In addition, phenol is much cheaper than benzenethiol. The method is well suited for the preparation of p-lactones from symmetrical and unsymmetrical ketones. In addition to 3,3-dimethyM-oxaspiro[3.5]nonan-2-one, ( )-3-ethyl-1-oxaspiro[3.5]nonan-2-one and (3R, 4R )- and (3R, 4S )-4-isopropyl-4-methyl-3-octyl-2-oxetanone were prepared by this procedure in high yields (Notes 11 and 12). In the case of unsymmetrical ketones the less sterically crowded diasteroisomer is formed preferentially. With aldehydes as the carbonyl component the yields are unsatisfactory, because of the competitive formation of 1,3-dioxan-4-ones.6... 

CsHuN, Ethanamine, A-ethyl-A-methyl-tungsten complex, 26 40, 42 C6HF5, Benzene, pentafluoro-gold complexes, 26 86-90 C H4I2, Benzene, 1,2-diido-iridium complex, 26 125 CJT, Phenyl platinum complex, 26 136 C,H,N, Pyridine osmium complex, 26 291 OHtS, Benzenethiol osmium complex, 26 304 QH7P, Phosphine, phenyl-cobalt-iron complex, 26 353 QH 1-Butyne, 3,3-dimethyl-mercury-molybdenum-ruthenium complex, 26 329-335 C6H 4P, Phosphine, triethyl-platinum complex, 26 126 platinum complexes, 26 135-140 CsHisPO, Triethyl phosphite iron complex, 26 61... 

In a 500-mL. round-bottomed, four-necked glass reactor, fitted with an efllcient mechanical stirrer, thermometer. sintered gas inlet, and a condenser (cooled to — 40 C). was charged the benzenethiol 7 (0.2 mol), finely crushed NaOH (20 g, 0.5 mol). tris[2-(2-methoxyethoxy)ethyl]amine (TDA-I 3.2 g, 0.01 mol), and solvent (TCB or toluene. 200 mL). This mixture was vigorously stirred while chlorodifluoromethane (8) was bubbled through the solution. A noticeable exothermy was observed during the first few min. Then, the medium was heated up to the desired temperature (vide supra) and maintained there for the time indicated, whilst passage ofS was continued. The progress of the reaction was monitored by GC analysis. 

Nakazumi H, Wanatabe S, Kitaguchi T, Kitao T (1990) Intermediates formed in the reaction of benzenethiol or tert-butythio benzene with ethyl benzoylacetate in polyphosphoric acid. Bull Chem Soc Jpn 63 847-851... 

The thiol (SH) group is introduced by reaction with potassium ethyl xanthate followed by acid hydrolysis. The phenylsulfanyl (phenylthio, SPh) group results from reaction with benzenethiolate ion. Sodium disulfide, Na2S2, yields diaryl disulfides. The arsonic acid group is introduced using Bart s reaction, in which a diazonium salt is reacted with sodium arsenite in the presence of a Cu(II) salt (Scheme 8.23). 

A series of novel 2-amino-6-aryl-9-[2(phosphonomethoxy)ethyl] purine bis (2,2,2-trifluoroethyl) esters (404) has been synthesized by satisfactory regioselec-tive alkylation of 2-amino-6-chloropurine (405) with the bis(tri-fluoroethyl)(2-iodoethoxy)methylphosphonate(406), followed by exchanging the chlorine atom in the resultant intermediate (407) for various substituted and unsubstituted benzenethiols and naphthalenethiols. 6-Phenylthio- and 6-(methoxyphenyl)thio-derivatives showed potent Hepatits B-specific antiviral activity in vitro, and 9[2-(phosphonomethoxy)ethyl] adenine and 9[2-(phosphonomethoxy)ethyl] 2,6-diaminopurine have a broad spectrum of activity against viruses (Scheme 105). ... 

Michael addition of benzenethiolate to 4-f-butyl-l-cyanocyclohexene gives only products containing an axial PhS group the same result was obtained from ethyl 4-r-butylcyclohexene-l-carboxylate. In contrast, the addition of diethyl sodiomalonate gave only the equatorial malonate group under thermo-... 

It is highly probable that the initial step in the overmercaptalation of 27 involves formation of a 2,3-acyloxonium ion however, formation of the 1,2-episulfonium ion 28 as an intermediate in the replacement of the 2-hydroxyl group has been established130 through the conversion of 27 into 3,4,5,6-tetra-0-benzoyl-2-S-ethyl-2-thio-D-man-nose ethyl phenyl dithioacetal (34) by the action of benzenethiol and an acid catalyst. The presence of an ethylthio group on C-2 in 34 was further established by conversion of 34 into 3,4,5,6-tetra-O-benzoyl-2-S-ethyl-2-thio-D-mannose dimethyl acetal. 

Sodium benzenethiolate reacted with 6,6-dimethyl-2-vinyl-5,7-dioxaspiro[2.5]octane-4,8-dione (16) to give the 1,5-addition product only. When ethyl trani-6-(l-heptenyl)-2-oxo-bicyclo[3.1.0]heptane-l-carboxylate (18, R = Et) was treated with potassium benzenethiolate it was converted stereospecifically to the corresponding trawj -cyclopentanone derivative 19 (R = Et) with a defined configuration at the a-carbon atom of the side chain. This reaction proved to be useful for the stereoselective synthesis of prostaglandins. ... 

Benzaldehyde, 100, 105, 154, 175, 336 Benzamide, 320 Benzene, 134, 154, 198, 286 Benzenesulfenyl chloride, 182 Benzenesulfinic acid sodium salt, 18 Benzenesulfonamide, 18 Benzenesulfonyl azide, 17—18 Benzenesulfonyl bromide, 18 Benzenesulfonyl chloride, 17 N-Benzenesulfonylformimidic acid ethyl ester, 18-19 Benzenethiol, 182 Benzhydrol, 238 Benzil, 312 Benzimidazole, 126 2,1-Benzisothiazole, 290 Benzobicyclo[2.2.2]octadiene, 46 Benzocyclobutadiene, 227 Benzohydroquinones, 60 Benzoic acid, 175... 

The syntheses of the metal-benzenethiolate complexes are accomplished by a ligand substitution reaction between the appropriate O-ethyl dithiocarbonate complexes and potassium benzenethiolate, KSPh. In the original report on the syntheses of the [M(SPh)4]2 complexes,1 the bis(3,4-dimercapto-cyclobutane-1,2-dione) [dithiosquaric acid] metal complexes were used in the ligand substitution reactions. The rather involved synthesis of the dithiosquarate ligand,2 using expensive starting materials, prompted us to develop new synthetic procedures which utilize the readily available, inexpensive O-ethyl dithiocarbonate complexes.3... 

The scope of the reactions of 5-nitro-3-thienylethyl chloride and acetate with the lithium salt of 2-nitropropane to give (83) (cf. this series, Vol. 2, p. 80) has been investigated. The cyano-group was not found to be sufficiently active, since 4-cyano-2-thienyl-methyl and -ethyl chlorides only gave O-alkylated products by an mechanism. The iSn(AEAE) reaction also occurred between benzenethiolate and 4-nitro-2-thienylmethyl acetate, and a moderate yield of 4-nitro-2-thienylmethyl phenyl sulphide was obtained. 

Butylphenyl thioether is first prepared by the interaetion of sodium benzenethiolate and butyl chloride. The resulting product on treatment with benzoyl ehloride and aluminum chloride yields butyl-p-benzoyl phenyl thioether. This on reaction with zinc and sodium hydroxide and earbonyl ehloride yields an intermediate. The intermediate on treatment with thiourea, sodium hydroxide, 2-dimethyl amine ethyl chloride and hydrochloric acid gives rise to the desired eompoimd. 

Lithium, methyl-, 55, 7,10 Lithium, phenyl-, 55,11 Lithium phenylthio(alkyl)cupiates, 55,122 LITHIUM, phenyllhio(fert-butyl)cuprate [Lithium, phenylthio(l,l-dimethyl-ethyl)cuprate), 55,122 Lithium, 1-propenyl-, 55,111 LITHIUM, (E)-l-propenyl-, 55, 103 Lithium thiophenoxide [Benzenethiol, lithium salt], 55,122... 

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