Ethyl-2-naphthyl sulfide

Naphthyl phenyl sulfide is desulfurized to naphthalene on refluxing with lithium aluminum hydride and titanium tetrachloride, and 1-naphthyl ethyl sulfide and 1-naphthyl isopropyl sulfide are converted to naphthalene on treatment with ethanethiol and anhydrous aluminum chloride (equation 83). ... 

Methyl- or 2-ethyl-benzo[Z> ]thiophenes are conveniently prepared by treatment of 2-benzo[6]thienyllithium with the appropriate alkyl sulfate <70AHC(11)177). Clemmensen or Wolff-Kishner reductions of the 2-acylbenzo[Z>]thiophenes are useful, but since acylation produces a mixture of the 2- and 3-acyl isomers (Section 3.14.2.4), these must be separated. Cyclization of phenyl phenacyl sulfide with hydrofluoric acid leads exclusively to 2-phenyl-benzo[6]thiophene, and 3-phenylbenzo[6]thiophene can be rearranged to the 2-isomer in hydrofluoric acid (Section 3.15.2.3.2). Aromatization of 2-cycIohexenylbenzo[6]thiophene, obtained by condensation of the 2-lithio reagent with cyclohexanone, gives 2-phenyl-benzo[6]thiophene, and the reaction is adaptable to the 2-(l-naphthyl) derivative also. 

This general reaction can be used for preparing other un-symmetrical thioureas when the desired cyanamides can be obtained. The submitter has also prepared l-methyl-l-(l-naph-thyl)-2-selenourea, m.p. 174-175° with decomposition, and l-ethyl-l-(l-naphthyl)-2-selenourea, m.p. 168-170° with decomposition, by substitution of hydrogen selenide for hydrogen sulfide. 

Methyl (99%) and ethyl 2-naphthyl sulfide (68%), (2-naphthylthio)acetic acid (87%), and 2-naphthyl phenyl sulfide (43%) have been prepared by the same method. 

Dimethyl sulfide N,N -Di-P-naphthyl-p-phenylenediamine 2,4-Dinitrophenyl phenyl sulfide Ethyl-N-butylamine 2-Ethylhexanal 2-Ethylhexenal 2-Ethyl-2-hexenal Ethyl vinyl ketone Formamide Glyceryl-a-monochlorohydrin... 

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