Benzyl- phenyl sulfoxides

In the reaction of 88 with /(-phenethyl bromide, l-phenethyl-3-phenylpropyl methyl sulfoxide and bis-3-phenylpropyl sulfoxide, besides 3-phenylpropyl methyl sulfoxide are obtained118. Sulfoxides, bearing a /1-hydrogen to the sulfmyl function, give olefins upon thermolysis. Utilizing this reaction, Trost and Bridges120 alkylated benzyl phenyl sulfoxide, 3,4-methylenedioxybenzyl phenyl sulfoxide, phenylthiomethyl phenyl sulfoxide, phenylsulfinylmethyl phenyl sulfoxide and cyanomethyl phenyl sulfoxide with alkyl, allyl and benzyl halides and subjected these sulfoxides to thermolysis, obtaining olefins in one-pot processes. 

A 25 mL round-bottomed flask equipped with a magnetic stirrer bar was charged with WO3 (0.012g, 0.05 mmol), (DHQD)2-PYR (0.088g, 0.1 mmol) and racemic ( )-benzyl phenyl sulfoxide (0.216g, 1 mmol) in THF (2mL). To this reaction mixture was added aq. 30 % H2O2 (0.17 mL, 1.5 mmol) at 25 °C. The reaction mixture was stirred at 25 °C for 20 h. 

NMR of crude product) and finally elution by chloroform afforded pure benzyl phenyl sulfoxide 2d in 86% yield, mp 123 °C. 

Steroidal sulfides are converted into optically active sulfoxides by Ca-lonectria decora [1052] and by Rhizopus stolonifer [1048]. Aspergillus niger transforms benzyl phenyl sulfide into optically active benzyl phenyl sulfoxide in 23% yield and into benzyl phenyl sulfone in 9% yield [1048]. 

Benzyl phenyl sulfoxide 600 Benzyl phenyl sulfide (52 g) is dissolved in acetone (250 ml), filtered, and treated with 30 % hydrogen peroxide (40 g), then thoroughly shaken and set aside for 72 h. The acetone is evaporated and the residue is caused to crystallize by moderate cooling and then recrystallized (yield 40 g m.p. 122-123°) from 60% ethanol. 

CONJUGATE ADDITION Alkylmethyl-magncsiocuprates. 2-Carboethoxyl-benzyl phenyl sulfoxide. Cyanodiethyl-aluminum chloride. 1-Cyclopropyl-l-tiimethylsilyloxyethylene. Lithium 1,3-butadiene-l-olate. Lithium dimethyl-cuprate. Magnesium ethyl malonate. Potassium carbonate. Tri-n-butyl-stannyllithium. Trimethylzinclithium. 

Activation of carbon—hydrogen bonds in benzyl phenyl sulfoxides catalysed by palladium may lead to dibenzothiophene derivatives (39). lodoarenes and silver salts are required as additives, and product formation requires several consecutive catalytic cycles. The copper-catalysed conversion of bisaryloxime ethers to 2-arylbenzoxazoles is likely to involve complexation of the catalyst at... 

When the chiral center is tricoordinate, as is the case for sulfoxides sulfonium salts, and phosphines, then a phantom atom of atomic number zero is taken to occypy the lowest-priority site of a presumed tetrahedral atom. Application of the sequence rule in the usual manner allows the assignment of the R configuration to the benzyl phenyl sulfoxide enantiomer and the 5 configuration to the methylal-lylphenylphosphine enantiomer shown in Scheme 2.1. 

Along with C—N and C—O bond formation reactions, transition-metal-catalyzed C—S bond formation reaction has also been developed. However, the reaction has scarcely been applied to the synthesis of dibenzothiophenes. In this context, Samanta and Antonchick reported the palladium-catalyzed synthesis of 1-formyldibenzothiophene 80 from benzyl phenyl sulfoxides 78 (Scheme 23.30) [41]. 

The palladium-catalyzed double C-H activation of simple benzyl phenyl sulfoxides to synthesize dibenzothiophenes (DBTs) was described by Antonchick and coworkers (Scheme 4.3) [7]. They proposed that the sulfoxide functionalized as a directing group to undergo the first ortho-C-H activation in the benzyl phenyl... 

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