4-methoxyphenyl phenyl sulfid

Benzenesulfenyl diloride added dropwise at room temp, under N2 in the dark during 0.5 hr. to anisole containing a little Fe-powder 4-methoxyphenyl phenyl sulfide. Y 78%. F. e. s. T. Fujisawa et al., Tetrah. Let. 1968, 5071. 

Methoxynaphthalene, 223 p-Methoxyphenol, 99 4-Methoxyphenyl-4-allyloxy benzoate, 537 Methoxyphenylisocyanate, 306 4-Methoxyphenylsulfonyl chloride, 253 Methyl-(4-anilino-phenyl) sulfide, 187, 188 A -(a-Methylbenzyloxy)-2,2,6,6-tetramethylpiperidine, 41 p-Methylbenzyltrimethylammonium hydroxide, 70... 

Preparation of various enantiomerically pure sulfoxides by oxidation of sulfides seems feasible in the cases where asymmetric synthesis occurs with ee s in the range of 90% giving crystalline products which can usually be recrystallized up to 100% ee. Aryl methyl sulfides usually give excellent enantioselectivity during oxidation and are good candidates for the present procedure. For example, we have shown on a 10-mmol scale that optically pure (S)-(-)-methyl phenyl sulfoxide [a]p -146 (acetone, o 1) could be obtained in 76% yield after oxidation with cumene hydroperoxide followed by flash chromatographic purification on silica gel and recrystallizations at low temperature in a mixed solvent (ether-pentane). Similarly (S)-(-)-methyl o-methoxyphenyl sulfoxide, [a]p -339 (acetone, o 1.5 100% ee measured by HPLC), was obtained in 80% yield by recrystallizations from hexane. 

Araki et al. have found that La wesson s reagent, 2,4-bis(4-methoxyphenyl)-l,3-dithiaphos-phetane-2,4-disulflde, provides a convenient one-step conversion of mesoionic olates to mesoionic thiolates <88BCJ2977>. Thus 3-phenyl-1,2,3,4-thiatriazolium-5-olate (170) was converted to (171) in high yield by refluxing for 50 min in benzene (Equation (14)). This eompound had previously been prepared from compound (161 R = Ph) by treatment with sodium sulfide in aqueous dimethyl-formamide at room temperature <79JCS(Pi)732>. 

Sulfide 130 can be alternatively prepared in 93% yield by treatment of 3-phenyl-l,2,3,4-thiatriazolium-5-olates 38 with Lawesson s reagent (2,4-bis(4-methoxyphenyl)-l,3-dithiaphosphetane-2,4-disulfide) 129 (Equation 7) <1988BCJ2977>. 

C16H25N2O2PS2, 3,4-Bis(t-butyl)-2-(p-methoxyphenyl)-1,3,4,2-thia-diazaphospholidin-5-one 2-sulfide, 45B, 741 C16H25O2P, 1,4-Dioxa-5-phenyl-6,6,7,8,8-pentamethyl-5X -phosphaspi-ro[3.4]octane, 44B, 623... 

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