NeOPHYL CHLORIDE

NEOPHYL CHLORIDE [Benzene (chloro-tert-butyl)-]... 

The reaction mixture is then transferred to a 1-1. separatory funnel, and the sulfuric acid layer is removed. The remaining benzene solution is then washed with four 200-ml. portions of distilled water (Note 3). In this step the amber color disappears and the liquid becomes colorless. The benzene solution is dried with anhydrous sodium sulfate and transferred to a 1-1. distilling flask. The benzene is removed by distillation under a pressure of about 45 mm. The liquid residue is poured into a 500-ml. flask and distilled through a 40-cm. Vigreux column under reduced pressure. The yield of neophyl chloride boiling at 97-98°/10 mm. is 262-275 g. (70-73%) (Notes 4 and 5) ... 

Naphthylacetamide, 32, 94 a-Naphthylcyanamide, 31, 20 -Naphthyl ethyl ether, 32, 97 -Naphthyl methyl ether, 32, 100 Neophyl chloride, 32, 90 Nicotinamide, 30, 3 Nicotinonitrile, 1,2-dihydro-... 

Neophyl chloride in 13—75% current yield forms f-butylbenzene (94%) and isobutylbenzene (6%) as side product by rearrangement of the intermediate neO phyl radical 487>. Reduction of monobromomaleic acid at pH 0—4 yields up to 50% of the dimer 163 (Eq. (228)). With increasing pH the amount of dimer... 

Neopentyl chloride (101a) and neophyl chloride (101b) react with Ph2P ions in liquid ammonia forming high yields of the substitution product 102a and 102b (equation 74). 

Figure 19. Correlation of solvolysis rate constants for neophyl chloride (46, X - Cl) at 50° and Y. O, EtOH/HjO , MeOH/HjO O, dioxane/H20 , AoOH/H20 9, Ac0H/HCO2H. (From Fainberg and Winstein, 1957 and reproduced by permission of the American Chemical Society.)...

Naphthyl acetic acid naphthyl acetamide Naphthyl 1 acetonitrile Naphthyl acetic acid 1-Naphthylamine antu, naptalam Neophyl chloride fenbutatin oxide Nicotinic acid diflufenican p-Nitroaniline DCNA (dicloran)... 

Naphthylacetamide, 32, 94 a-Naphthylcyanamide, 31, 20 /3-Naphthyl ethyl ether, 32, 97 a-NAPHTHYL isothiocyanate, 36, 56 /3-Naphthyl isothiocyanate, 36, 57 -Naphthyl methyl ether, 32, 100 a-Naphthylphenylacetylene, 34, 43 a-Naphthylthiourea, 36, 56 Neophyl chloride, 32, 90 Nickel, dicyclopentadienyl-, 36, 35 Nicotinamide, 30, 3 33, 52 Nicotinic acid, 6-hydroxy-, 36, 44 Nocotinonitrile, 33, 52... 

The new route began with benzene and neophyl chloride to afford a low cost source for... 

Evidence for a surface-bound radical was also provided by work of Ruchardt et al. [59]. Reaction of neophyl chloride 55 with magnesium led, after carbonylation, to acid 61 in 65% yield, without any contamination by acid 60, which could have arisen by rearrangement of radical 56 to radical 57 (Scheme 24). 

CsH5C(CHs)>CH>1. Neophyl iodide, prepared (59) from neophyl chloride (58) reacted with K3Co(CN).-> in the same way, except that 12 ml. of benzene were added to disperse the halide, and reaction time was 20 hours. The infrared spectrum of the light brown solid product isolated exhibited CN stretch bands at 2125 and 2089 cm." Acidification followed by alkali treatment yielded neophyl cyanide (infrared and PMR analysis). 

Neophyl Chloride. (2-Chloro-l, I-dimethyiethyi 1-benzene 1-chloro-2-methyl-2-phenytpropane (jj-chloro-rert-butyl)benzcne. C 0H[(O mol wt 168.67. C 71.21%. M 7.77%, Cl 21.02% Prepn (68% yield) from benzene and methallyl chloride in the presence of coned sulfuric acid ... 

Benzene, (2-chloro-1,1-dimethylethyl)- (p-Chloro-a,a-dimethyl)ethylbenzene (p-Chloro-t-butyl)benzene (2-Chloro-1,1-dimethylethyl)benzene p,p-Dimethylphen-ethyl chloride EINECS 208-197-7 2-Methyl-2-phenyl-propyl chloride Neophyl chloride NSC 54159. Liquid bp = 223 , bpi8 = 105" very soluble in EtOH, EtzO, MezCO, CeHe. 

Another reaction of radicals is rearrangement. Radicals are generally less susceptible to rearrangement than are carbocations, and the 1,2 hydrogen or carbon shifts seen with carbocations are not observed with radicals. However, apparent phenyl migration has been observed (Scheme 4.37). Treatment of neophyl chloride with phenyhnagnesium bromide and cobaltous chloride produced isobutylbenzene... 

It is generally felt that other Kharasch reactions involve radical intermediates, since 2,3-dimethyl-2,3-diphenylbutane is formed when cumene is present, and rearrangement products are observed in the neophyl chloride system, although some of the latter might arise from the carbanion rearrangement reactions described in Section II, D. 

Neophyl Radicals 1962. A few years later, the reaction of neophyl chloride (I) with magnesium was studied [24] in diethyl ether. 

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