Ethyl phenyl sulfide

Yu and coworkers reported the design and synthesis of a series of conductive OPEs possessing a ferrocene and thiol at each terminus [101]. The solubility is achieved by substitution at the phenyl groups with methyl and propoxy substituents (67). Several new reactions for preparing novel arenethiol-protected compounds (e.g., 2-(4-pyridinyl)ethyl-4 -(ethyl)phenyl sulfide) are reported. 

Thiol esters can be reduced to sulfides or aldehydes. Alone generated from lithium aluminum hydride and boron trifluoride etherate [1099] or aluminum chloride [1100] in ether reduced the carbonyl group to methylene and gave yi-9y /o yields of sulfides. Phenyl thiolbenzoate failed to give the sulfide, and phenyl thiolacetate gave only an 8% yield of ethyl phenyl sulfide [1100]. 

Ethyl 3 phenylpropenoate, AT50 Ethyl phenylpropiolate, AT22 Ethyl phenylpropynoate, AT22 Ethyl phenyl sulfide, ANY3 Ethyl phenyl thioether, AN73... 

The photoinitiated reaction of iodobenzene with ethanethiolate ion in liquid ammonia affords not only ethyl phenyl sulfide but also benzenethio-late ion, trapped as the benzyl derivative (Sch. 7) [51]. 

Ethyl phenyl sulfide is lithiated mainly in the ortho position, but with significant amounts of meta and para lithiation and substitution products. Superbases, on the other hand, prefer to deprotonate alkylthio benzenes at benzylic or a-positions, rather than on the ring.209 210... 

Chloro-l-(trifluoromethyl)ethyl Phenyl Sulfide (26) Typical Procedure ... 

Oxidation of diphenyldisulfide in a mixture of glacial acetic acid and concentrated hydrochloric acid at a platinum anode yielded benzenesulfonic acid ethyl phenyl sulfide yields benzenesulfonic acid [226]. 

Ethyl phenyl sulfide can be oxidized to the sulfoxide in 97% yield using 30% aqueous hydrogen peroxide in l,l,l,3,3,3-hexafluoro-2-propanol.239 No sulfone is formed. The fluorinated alcohol (bp 59°C) is recovered by distillation for use in the next run. 

Benzyl methyl sulfide Ethyl phenyl sulfide... 

A soln. of thiophenol, ethyl bromide, Na2C03, and a little dichloro[bis(diphenylphos-phino)methane]platinum(II) in acetone boiled overnight ethyl phenyl sulfide. Y 75%. F.e. incl. 1,3-dithioethers, also mercaptals from 1,1-dihalides, s. P.C. Bulman Page et al.. Tetrahedron Letters 29, 4477-80 (1988). 

With (salalen)Al complex 33 as the chiral catalyst, the reactions of aryl methyl sulfides proceeded smoothly to give the sulfoxides in high yields with excellent enantioselectivity, irrespective of the electronic nature and the location of the substituent on the aromatic ring (Scheme 19.38). Ethyl phenyl sulfide is also a good substrate for the oxidation which gave the sulfoxide in 80% yield with 91% enantiomeric excess. 

Thiophenetole (ethyl phenyl sulfide, 213) by prolonged heating with chlorosulfonic acid at 150-160 °C gave ethyl pentachlorophenyl sulfide 214 (Equation 68). 

Ethyl phenyl sulfide, by prolonged heating with excess chlorosulfonic acid, was chlorinated to give ethyl pentachlorophenyl sulfide (see Chapter 4, p 76). 

The screening of a metagenomic library derived from loam soil afforded a novel two-component SMO, which has been heterologously expressed in E. coli [52], This biocatalytic system was able to perform selective sulfoxidations of alkyl aryl sulfides, providing the recovered (R)-sulfoxides with good to high selectivities and moderate conversions after 16h. Ethyl phenyl sulfide was the best substrate for this enzyme, as the final sulfoxide was obtained with 92% ee. It therefore represents an interesting SMO alternative. 

A variety of methods for the reduction of sulfoxides to sulfides are available. PI3 rapidly reduces aryl alkyl and dialkyl sulfoxides and selenoxides, usually at —78 °C (eq 3). For example, treatment of ethyl phenyl sulfoxide with 1 equiv of PI3 (CH2CI2, -78 °C, 15 min) affords ethyl phenyl sulfide in 91% yield. Others have successfully employed this procedure. Dialkyl sulfoxides generally react in somewhat lower yield. A phenyl vinyl sulfoxide (eq 3, entry c) requires ambient temperatures to react. Selenoxides behave similarly, and P2I4 can usually be used in place of PI3. Treatment of decyl phenyl selenone with PI3 (CH2CI2, 0 °C, 30 min) affords a mixture of the reduced product, decyl phenyl se-lenide (69%), and the substitution product, n-decyl iodide. ... 

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