Ethylene dithiotosylate

C. Ethylene Dithiotosylate. To 200 ml. of ethanol containing 10-20 mg. of potassium iodide is added 45.3 g. (0.2 mole) of potassium thiotosylate and 18,8 g. of ethylene dibromide. The mixture is refluxed with stirring for 8 hours in the dark and under a nitrogen atmosphere. The solvent is removed, and the resulting white solid is washed with a mixture of 80 ml. of ethanol and 150 ml. of water. After decantation, the solid is washed three times with 50-ml. portions of water and then recrystallized from approximately 150 ml. of ethanol to yield 28.7 g. of crude product, m.p. 72-75°. Three reerystallizations from a mixture of ethyl acetate and ethanol afford 24 g. (60%) of white crystals, m.p. 75-76° (Note 9). 

Trimethylene dithiotosylate can react with activated methylene groups, enamines, or hydroxyethylene derivatives of carbonyl compounds to form dithiane derivatives. Ethylene dithiotosylate undergoes similar reactions to form dithiolanes.3 6... 

The procedure for the preparation of a dithiolane from a hydroxy-methylene derivative of a ketone and ethylene dithiotosylate (ethane-1,2-dithiol di-p-toluenesulfonate) can be varied to produce dithianes when the latter reagent is replaced by trimethylene dithiotosylate.8,4 The dithiotosylates also react with enamine derivatives to produce dithiaspiro compounds.4,5... 

A 300-ml., one-necked flask is equipped with a reflux condenser, to the top of which a nitrogen inlet tube is attached. The flask is charged with 3.85 g. (0.03 mole) of 2-hydroxymethylenecyclohexanone (Note 1), 10 g. (0.025 mole) of ethylene dithiotosylate (Note 2), and 10 g. of potassium acetate in 150 ml. of methanol, and the mixture is refluxed for 3 hours with stirring and under nitrogen. The solvent is removed from the reaction mixture on a rotary evaporator, and the residue is extracted with three 50-ml. portions of ether. The combined ethereal extracts are washed with cold aqueous 2N sodium hydroxide (Note 3) until the... 

Ethylene dithiotosylate, TsS(CH2)2STs, can be used in an analogous manner. 

Ethylene dibromide, 126-127 Ethylene dithiotosylate, 540 Ethylene glycol, 69 Ethylene ketals, 322 Ethylene oxide, 41,231-232 Ethylenethioketals, 75,79 Ethyl 3-ethyl-5-methyl-4-isoxazolecarboxyl-ate, 232... 

Details for the preparation of trimethylene dithiotosylate and of ethylene dithiotosylate have been published. Use of the former reagent for preparation of dithianes from enamines and use of the latter reagent for preparation of... 

A mixture of 2-hydroxymethylenecyclohexanone, ethylene dithiotosylate, and K-acetate in methanol stirred and refluxed 3 hrs. under Ng -> 1,4-dithiaspiro-[4.5]decan-6-one. Y 45-55%. R. B. Woodward, I. J. Pachter, and M. L. Schein-baum, Org. Synth. 54, 37 (1974) from enamines cf. ibid. 54, 39 2-acyl-l,3-di-thianes by mild cleavage of / -diketones, without K-acetate, s. R.J. Bryant and E. McDonald, Tetrah. Let. 1975, 3841. 

Bis-4-methylbenzenesulphonyl [2225-23-2]. Ethylene dithiotosylate. S,S -7,2-Ethanediyl-4-methylbenzenesulfonothioate Cryst. (EtOH/EtOAc). 

EthyIenediphosphonic acid, see E-00026 Ethylenedithiodiacetic acid, E-00080 Ethylene dithiotosylate, in E-00028... 

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