Benzenethiol lithium salt

Thiophenol, lithium salt [Benzenethiol, lithium salt], 55, 122 Toluene, 4-bromo- [Benzene, 1 bromo 4 methyl-], 55, 49... 

Benzenesulfonyl chloride, 4-methyl- [p-Tol-uenesulfonyl chloride], 55, 57, 59 Benzenethiol [Phenol, thio-], 55, 122 Benzenethiol, copper(I) salt [Thiophenol, copper(I) salt], 55, 123 Benzenethiol, lithium salt [Thiophenol, lithium salt], 55, 1 22 Benzoic acid, 2-amino- [Anthramlic acid], p bromination of, 55, 23... 

Benzenethiol, copper(I) salt, 55, 123 Benzenethiol, lithium salt, 55, 122... 

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... 

The complex Os(SCl0Hl3)4(CNMe) is made from OsCl3, the lithium salt of 2,3,5,6-tetramethyl-benzenethiolate and 2,3,5,6-tetramethylphenyl sulfide it is green-yellow. The X-ray crystal structure of the ruthenium salt shows it to be trigonal bipyramidal, with the acetonitrile in the axial position. The osmium complex is isomorphous it would seem therefore to be the only example so far reported of a trigonal bipyramidal osmium(IV) complex. In an attempt to make a complex of lower coordination number 2,4,6-triisopropylbenzenethiolate (SC15H23) was used but the complex was still pentacoordinate, i.e. Os(S15H23)4(MeCN).719... 

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. 

Migration of trialkylsilyl and germanyl groups from sulphur to aromatic carbon was also observed . Lithiation of 4-bromo-S-trimethylsilyl-benzenethiol (6) yields the lithium salt of 4-trimethylsilylbenzenethiol (7). The mechanism has not been investigated and it has not been established whether an intra- or intermolecular process is involved. 

This method, using ethanethiolate, has been extended to esters. The cleavage of methyl esters by lithium propanethiolate in HMPA, an 8 2 reaction, has been reported. The lithium salt reacts very much faster than the sodium salt. The benzenethiolate and propanethiolate anions have... 

A comparison of the suitability of solvents for use in Srn 1 reactions was made in benzenoid systems46 and in heteroaromatic systems.47 The marked dependence of solvent effect on the nature of the aromatic substrate, the nucleophile, its counterion and the temperature at which the reaction is carried out, however, often make comparisons difficult. Bunnett and coworkers46 chose to study the reaction of iodoben-zene with potassium diethyl phosphite, sodium benzenethiolate, the potassium enolate of acetone, and lithium r-butylamide. From extensive data based on the reactions with K+ (EtO)2PO (an extremely reactive nucleophile in Srn 1 reactions and a relatively weak base) the solvents of choice (based on yields of diethyl phenylphosphonate, given in parentheses) were found to be liquid ammonia (96%), acetonitrile (94%), r-butyl alcohol (74%), DMSO (68%), DMF (63%), DME (56%) and DMA (53%). The powerful dipolar aprotic solvents HMPA (4%), sulfolane (20%) and NMP (10%) were found not to be suitable. A similar but more discriminating trend was found in reactions of iodobenzene with the other nucleophilic salts listed above.46 Nearly comparable suitability of liquid ammonia and DMSO have been found with other substrate/nucleophile combinations. For example, the reaction of p-iodotoluene with Ph2P (equation (14) gives 89% and 78% isolated yields (of the corresponding phosphine oxide) in liquid ammonia and DMSO respectively.4 ... 

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