1- Chloro-2-phenylethane

Both methyltriethylphosphonium fluoride and methyltributylphospho-nium fluoride have been prepared The latter generates benzyl fluoride from benzyl chloride in 80% yield and ethyl fluoroacetate from ethyl bromoacetate in 53% yield Methyltnbutylphosphonium fluoride converts 1-bromododecane to a 50 50 mixture of 1-fluorododecane and 1-dodecene Methyltnbutylphosphonium fluoride also quantitatively forms styrene from 1-bromo-1-phenylethane [26] Methyl-tnbutylphosphonium fluonde is the reagent of choice for the conversion of N,N dimethylchloroacetamide to its fluoride, but it is not able to convert chloro-acetonitnle to fluoroacetomtrile Methyltnbutylphosphonium fluoride changes chloromethyl octyl ether to the crude fluoromethyl ether in 66% yield The stereoselectivity of methyltnbutylphosphonium fluoride is illustrated by the reac tions of the 2-tert-butyl-3-chlorooxiranes [27] (Table 2)... 

As far as the reactions with benzyl chlorides are concerned (74), the oxidative addition of benzyl chloride and substituted benzyl chlorides to palladium atoms yields rj -benzylpalladium chloride dimers. The parent compound, bis(l,2,3-7 -benzyl)di-/i,-chloro-palladium(II), quantitatively adds four molecules of PEts by first forcing the rj -benzyl-iy -benzyl transformation, with subsequent breakage of the Pd-Cl bridges to form trans-bistPEtsKbenzyDchloroPddI). The spectral characteristics of the parent molecule are indicative of the allylic type of bonding. Similar i7 -benzyl compounds were formed from 4-methylbenzyl chloride, 2-chloro-l,l,l-trifluoro-2-phenylethane, and 3,4-dimethylbenzyl chloride. 

Optical activity retention is observed in the course of the formation of the Grignard reagent from optically active (+)-R-l-chloro-l-phenylethane and Mg in Et20.124 Treatment of the latter with Mg in EtzO and then with Me3COD gives 88% (-F)-S-PhCHDMe in 6.2% optical yield.124... 

Table 9.1). The rate of dehydrobromination from the intermediate bromoalkenes follows the pattern 2-bromoalkenes > Z-l-bromoalkenes > E- -bromoalkenes the corresponding chloro derivatives react more slowly. For optimum yield, the reaction temperature should be <100°C to reduce decomposition of the catalyst, and the concentration of base should be kept low to prevent isomerization of the resulting alkynes. [3-Elimination of HBr from 1,2-dibromo-1 -phenylethane can be controlled to yield 1-bromo-l-phenylethene in 83% yield [15]. The addition of alcohols and diols have a co-catalytic effect on the elimination reaction, as the alkoxide anions are transferred more effectively than the hydroxide ions into the organic phase [13]. 

Uses Intermediate in production of styrene, acetophenone, ethylcyclohexane, benzoic acid, 1-bromo-l-phenylethane, 1-chloro-l-phenylethane, 2-chloro-l-phenylethane, p-chloroethylbenz-ene, p-chlorostyrene, and many other compounds solvent in organic synthesis. 

In the case of a chloro, thio, or dimethylamino substituent, the hydrogen-bonded ring does not form, and the VCD due to C H stretching is weak or absent (20, 57). The characteristic methyl stretching VCD features observed for the a-phenylethane derivatives have also been interpreted in terms of currents generated about rings due to methyl-phenyl x interaction (57). 

The imidazole-containing hypnotic/injectable anesthetic agent etomidate (58) is synthesized from 1-amino-l-phenylethane starting with triethylamine mediated displacement with chloro-acetonitrile leading to secondary amine The -enantiomer... 

Reaction of AT-fluorobis(trifluoromethylsulfonyl)amine (Id) with alkenes gives various products, depending on the reaction conditions and the structure of the substrate. In solvents of higher nucleophilicity such as water, acetic acid, aqueous hydrochloric acid, and 70 % hydrogen fluoride/pyridine, a-fluorohydrins or their acetates, a-chloro-fl-fluoroalkanes or a,/ -difluoroal-kanes, e.g. 14. are obtained.146 Reaction of styrene and ( >l-phenylpropene with Id in dich-loromethane/acetic acid gives l-acetoxy-2-fluoro-l-phenylethane and -propane, in 92 and 99 % yield, respectively, the latter product in a ratio (erythrojthreo) 1 l.146... 

The elimination of hydrogen fluoride from vicinal fluorohalo compounds proceeds by a carb-anionic E1 cB mechanism, in which the acidity of the hydrogen plays a decisive role. The acidity of hydrogen is enhanced by the number of fluorine atoms in the /(-position,27-29 or by chlorine or bromine atoms in the a-position.30-39 For example, the rate of dehydrofluorination from 2-chloro-l,l,l-trifluoro-2-phenylethane (31) to give l-chloro-2,2-difluoro-l-phenylethene (32) is 85 times as high as the rate from l,l.l-trifluoro-2-phenylethane (33) to l,l-difluoro-2-phenyl-cthene (34).40... 

Chloro-1 -phenylethane Note This compound is not an aryl halide.)... 

Stereochemistry of the Sn I reaction of (S)-1 -chloro- I -phenylethane in acetic acid... 

According to Goddard, styrene reacted with nitryl chloride to yield 1,2-di-chloro-l-phenylethane in 70-80% yield. Another product l-chloro-2-nitro-l-phenyl-ethane was thought to be present, but could not be isolated. On distillation it decomposed, evolving HC1, and o- nitrostyrene was obtained. 

---