The Preparation and Properties of a Series of Alkyl Thiolacetates<sup>1</sup>

Wenzel, F.; Reid, E. Emmet

doi:10.1021/ja01285a037

Cited by 29 publications

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“…Suitable crystals for X-ray analysis were obtained by vapour diffusion from chloroform/n-hexane at 273 K. The 2-ethylsulfonyl acetyl chloride [1] was obtained following essentially literature procedures, i.e. from the reaction of thionyl chloride and 2-ethylsulfonyl acetic acid [2], which in turn, was obtained from the oxidation of the 2-ethylthioacetic acid [3] with hydrogen peroxide. Analysis: calc.…”

Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of 4'-methylphenyl-2-ethylsulfonyl thioacetate, C11H14O3S2

Zukerman-Schpector¹,

Olivato²,

T.³

et al. 2001

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of 4'-methylphenyl-2-ethylsulfonyl thioacetate, C11H14O3S2

Zukerman-Schpector¹,

Olivato²,

T.³

et al. 2001

Zeitschrift Für Kristallographie - New Crystal Structures

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“…and HIS COWORKERS (4,5) were the first to suggest that small weight-percentages of partitioning liquid on glass microbeads and small samples be combined to lower the column temperature and thereby decrease the chance of decomposing high-boiling substances. Glass beads were selected because their low specific surface area would decrease the amount of tailing due to adsorption by the support at the low7 liquid loadings employed.…”

Section: Hishtamentioning

confidence: 99%

“…(2,5), and the absence of the 12.42-micron band (2,4). A mixture of 10% 2,5-thioxylenol in 2,4-thioxylenol was obtained from the Consolidation Coal Co.…”

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confidence: 99%

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Quantitative Gas Liquid Chromatography of Thiocresols and Thioxylenols as Acetate Esters.

Croitoru¹,

Freedman²

1962

Anal. Chem.

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W cn z 0 b A rapid quantitative procedure is described for the preparation and gas liquid separation of the acetates of thiocresols and thioxylenols. The esters are prepared by reaction of the thiols with acetic anhydride in the presence of an organic base at room temperature under anhydrous conditions.s O m R I c thiocresols or thioxylenols I are very difficult to separate by fractionation. Similarity of boiling points and the reduced degree of hydrogen bonding (as compared to oxygen analogs) also render separation on gas liquid chromatographic columns impractical even with the use of capillary columns. The reactivity of these thiols toward metal may also be a significant factor. TT' e found that the silyl ethers (3) gave only partial separation and were highly unstable. The acetates, however, were readily prepared and gave quantitative separation.Thiocresol has been acetylated by acetyl chloride (1, 4) in nonaqueous media. The acetate has also been prepared by the action of acetic anhydride in the presence of aqueous base (4).A preparation of thiol acetates is described, using acetic anhydride as the acylating agent in the presence of an escess of triethylamine. The latter speeds up the reaction by combining with the liberated acetic acid. Reaction is almost instantaneous a t room temperature.The water-washed and dried product is readily separated chromatographically by using polypropylene sebacate on acid-washed Chromosorb IT. EXPERIMENTALReagents and Apparatus. The column was prepared by packing 157, by weight polypropylene sebacate on Chromosorb W, 60-to 80-mesh, into a 3.5 meter X 0.6 cm. i.d. aluminum tube.Polypropylene sebacate was purchased from Griffin and George, Ltd., 285 Ealing Rd., Alperton, Wembley, Middlesex, England.Celanese KO, 9 ester was obtained from the Celanese Corp. 0-, m-, and p-thiocresols were obtained pure from the Consolidation Coal Co. Triethylamine (boiling point 80" to 90" C.) was obtained from Matheson Coleman and Bell.2,&Thioxylenol was obtained pure from the Consolidation Coal Co. Its purity was confirmed by infrared analysis by observation of the presence of the 13.07-micron band, the absence of the 12.43-micron band (2,5), and the absence of the 12.42-micron band (2,4). A mixture of 10% 2,5-thioxylenol in 2,4-thioxylenol was obtained from the Consolidation Coal Co. The 2,6-thioxylenol had been removed by fractionation and its absence proved by the absence of the 13.07-micron band. Because of the proximity of the 2,4 and 2,s bands it was necessary to establish the composition of this mixture by gas chromatography of the acetates.Procedure. Thiocresols or thioxylenols (1 ml.), triethylamine (1 ml.), and acetic anhydride (1.5 ml.) are placed in a 60-ml. separatory funnel and shaken gently for 30 seconds. Distilled water (40 ml.) and benzene (0.5 to 2 ml.) are added. The benzene is added 0.5 ml. a t a time until the organic phase separates cleanly on top of the aqueous phase after gentle equilibration. The lower layer is withdrawn and rejected. Two more water washes are applied an...

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“…En utilisant des anhydrides d'acides aliphatiques, on abaisse fortement le risque de reactions secondaires avec le milieu rkactionnel sans toutefois compromettre les possibilit6s de reaction vis-8-vis des telluroph6nolates. I1 est bien connu en effet que les anhydrides se condensent aussi avec les alcoolates ou thioalcoolates [6] pour donner des esters ou thiolesters.…”

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Synthèses de tellurolesters

Piette¹,

Renson²

1970

Bulletin des Soc Chimique

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Bull. SOC. Chim. Belges, 79 (1970) 383-390 SYNTHESES DE TELLUROLESTERS J.L. PIETTE et M. RENSON Nous dkrivons une mtthode de prtparation des tellurolbenzoates d'aryle et des tellurolbenzoates d'alcoyle diffkremment substituts en vue d'ttudier en spectrographic infrarouge la position d u carbonyle de ce groupement fonctionnel. La synthkse mentionnee est baste sur la condensation de tellurophtnolates soit avec des chlorures d'acides aromatiques soit avec des anhydrides d'acides aliphatiques.La transposition du principe de la mtthode A des telluroalcoolates n'a pu &tre rkaliste avec succks.

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The Preparation and Properties of a Series of Alkyl Thiolacetates¹

Cited by 29 publications

References 0 publications

Crystal structure of 4'-methylphenyl-2-ethylsulfonyl thioacetate, C11H14O3S2

Crystal structure of 4'-methylphenyl-2-ethylsulfonyl thioacetate, C11H14O3S2

Quantitative Gas Liquid Chromatography of Thiocresols and Thioxylenols as Acetate Esters.

Synthèses de tellurolesters

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The Preparation and Properties of a Series of Alkyl Thiolacetates1

Cited by 29 publications

References 0 publications

Crystal structure of 4'-methylphenyl-2-ethylsulfonyl thioacetate, C11H14O3S2

Crystal structure of 4'-methylphenyl-2-ethylsulfonyl thioacetate, C11H14O3S2

Quantitative Gas Liquid Chromatography of Thiocresols and Thioxylenols as Acetate Esters.

Synthèses de tellurolesters

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The Preparation and Properties of a Series of Alkyl Thiolacetates¹