Tetramethylene sulfoxide

Tetramethylene sulfoxide (tetrahydrothiophen 1-oxide) [1600-44-8] M 104.2, b 235-237°, d 1.175, n 1.525. Shaken with BaO for 4 days, then distd from CaH2 under reduced pressure. 

Tetramethylene sulfoxide, TMSOTf, 4°, 4 h, 87% yield or Ph2SO, MeSiCl3 or SiCl4, TFA, 90-96% yield. The latter conditions also cleave the Acm, Bn, MeOBn, and MeBn groups. In all cases, disulfides are isolated. ... 

Trofimov and coworkers19 studied the yields of the radicals by ESR in the radiolysis at 100-110 K of diphenyl sulfoxide and tetramethylene sulfoxide. They found for tetramethy-lene sulfoxide a higher yield of radicals (G = 1.8) than for tetramethylene sulfide (G = 0.45). 

Korobeinikova and coworkers61 studied the extractability of petroleum sulfides (PSO) and their closest analog, tetramethylene sulfoxide (TMSO) upon gamma irradiation. The... 

The reaction is easy to carry out and workup was effected simply by the addition of dichloromethane and cyclohexane to the reaction mixture, filtration and evaporation of the solvents. Yields ranged from 77 to 96%, although in the case of tetramethylene sulfoxide, the product was contaminated with hexamethyldisiloxane. 

Treatment of the allylic sulfoxide 1227 a with diisopropylethylamine (DIPEA) or of 1227 b with N-trimethylsilyldiethylamine 146 and TMSOTf 20 leads in ca. 90% yield to the quaternary amino derivatives 1228 and 1229 and HMDSO 7 [36] (Scheme 8.15). Tetramethylene sulfoxide 1230 reacts with silylated thymine 1231 in the presence of three equivalents of TMSOTf 20 to give the 4 -thio-nucleoside analogue 1232 and HMDSO 7 [37]. Other silylated pyrimidine, pyridine, and purine bases react analogously with cyclic sulfoxides to give 4 -thio-nucleoside analogues [37, 37a, 38]. 

Tetramethylene glycol. See Butanediol Tetramethylene sulfoxide (TMSO) as PVDC solvent, 25 705 Tetramethylethylenediamine (TMEDA), 25 163... 

Also dipropyl sulfoxide [LnBra (161)], diphenyl sulfoxide [Lnl3 (155)], tetramethylene sulfoxide [LnCl3 (162), LnBrs (163), Lnls (164)], and thioxane oxide [LnCl3 (166), LnBrs (163), Lnl3 (266)]. 

In addition to these systematic studies of lanthanide sulfoxide complexes, with variation in both sulfoxide and anion, other more isolated reports are available. Lanthanide isothiocyanate complexes of the cyclic sulfoxides thioxane oxide (490) and tetramethylene sulfoxide (493) have been synthesized and complexes of the unusual potentially chelating ligand 2-(ethylsulfinyl)pyridine-V-oxide (63) described. Detailed studies of the solvation of lanthanide-shift reagents by Me2SO have also appeared (178,179). 

JV,JV-Di(n-butyl)acetamide 27.4 Diethylamine 162 Tetramethylene sulfoxide 6.4 2,4-Dime thylpyridine 19.1... 

PVDC dissolves at room temperature only in polar solvents like hexamethylphos-phoric acid amide or tetramethylene sulfoxide. Amorphous PVDC can also be dissolved in tetrahydrofuran. Above 125 °C PVDC decomposes by giving off hydrochloric acid. Under the influence of high energy irradiation, basic compounds and heavy... 

The basicity of the sulfoxide oxygen has been investigated by observing infrared shifts in protic solvents. ° In this way, it was shown that thietane 1-oxide is more basic than cyclobutanone, but less basic than tetramethylene sulfoxide (thiolane 1-oxide) or pentamethylene sulfoxide (thiane l-oxide). ° Toward phenol, the order of basicity is as follows thiolane 1 -oxide > diethyl sulfoxide > thiepan 1-oxide > dimethyl sulfoxide > thiane 1-oxide > 9-thiabicyclo[3.3.1]nonane 9-oxide > 7-thiabicyclo[2.2.1]heptane 7-oxide > thietane 1-oxide.ThepKaof the conjugate acid of thietane 1-oxide is — 1.92, as determined in aqueous sulfuric acid. =... 

Tetrahydrothiophene (tetramethylene sulfide) gives tetramethylene sulfoxide in 90% yield on refluxing for 2 h with tetrabutylammonium periodate [776]. The oxidation of tetramethylene sulfide with one equivalent of hydrogen peroxide at room temperature affords tetramethylene sulfoxide with two equivalents at refluxing temperature, tetramethylene sul-fone is obtained (equation 559) [164]. 

Solvent effects Birch reduction. 1,2-Dimethoxyethane (Glyme) and Dimethyl ether (see Naphthalene-Sodium), Dimethylformamide. Dimethyl sulfone. Dimethyl sulfoxide. Diphenyl sulfoxide. Ethylene glycol. N-EthylmorphoUne. Hexamethylphosphoric triamide. Methylal. Methylene chloride. Methyl ethyl ketone. N-Methyl-2-pyrrolidone. Nitrometbane. Nitrosyl chloride. Phenetole. Tetrahydrofurane. Tetramethylene sulfone. Tetramethylene sulfoxide. Triethanolamine. Triethyl phosphate. Trifluoroacetic acid,... 

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