204. s-Butyl chloride from n-butyl dichloroborinate and from n-butanol–hydrogen chloride

1962 ◽  
Vol 0 (0) ◽  
pp. 1099-1101 ◽  
Author(s):  
W. Gerrard ◽  
H. R. Hudson ◽  
W. S. Murphy
Keyword(s):  
Hydrogen Chloride ◽  
Butyl Chloride

The role of t-butyl chloride as an intermediate in the hydrogen chloride catalysed decomposition of t-butyl isopropyl ether

1973 ◽  
Vol 26 (4) ◽  
pp. 767
Author(s):  
NJ Daly ◽  
LP Steele ◽  
VR Stimson
Keyword(s):  
Hydrogen Chloride ◽  
Reaction Model ◽  
Alkyl Halides ◽  
Isopropyl Ether ◽  
Butyl Chloride ◽  
Runge Kutta Method ◽  
Pressure Time ◽  
The Family ◽  
Predictor Corrector

The possible formation of t-butyl chloride as an intermediate in the hydrogen chloride catalysed decomposition of t-butyl isopropyl ether according to the reactions is examined. Rates for t-butyl chloride decomposition and for the overall catalysed reaction are measured at 311�C and both a fourth-order Runge-Kutta method and Hamming's modified predictor-corrector method of numerical integration are used in computing the pressure-time curves due to the assumed reaction model using experi- mental values for k , and various assumed values for k2. It is found that no values for k2 can be found which generate the experimental curves and it is concluded that t-butyl chloride is not an intermediate of the reaction. If the hydrogen chloride catalysed decomposition of t-butyl isopropyl ether is typical of the family of catalysed decompo- sitions then alkyl halides generally have no role as intermediates.

Chlorination of 2,4,6-trichlorophenol in acidic aqueous medium

1985 ◽  
Vol 50 (8) ◽  
pp. 1842-1851 ◽  
Author(s):  
Petr Švec
Keyword(s):  
Reaction Mechanism ◽  
Aqueous Medium ◽  
Hydrogen Chloride ◽  
Reaction Medium ◽  
Model Experiments ◽  
Sulfuric And Hydrochloric Acids

The course of chlorination of 2,4,6-trichlorophenol (I) in water and approximately 20% sulfuric and hydrochloric acids has been investigated. In all these media the reaction gives primarily 2,4,6,6-tetrachloro-2,4-cyclohexadienone (II) which is subsequently chlorinated under formation of polychlorinated alicyclic ketones or isomerized to give the more stable 2,4,6,6-tetrachloro-2,5-cyclohexadienone (III), the precursor of further arising chlorinated 1,4-benzoquinones. The ratio of the arising polychlorinated alicyclic ketones to chlorinated 1,4-benzoquinones is significantly influenced by concentration of hydrogen chloride in the reaction medium. On the basis of model experiments, the reaction mechanism of exhaustive chlorination of 2,4,6-trichlorophenol has been suggested.

Preparation of Chloro and Sulfanyl Derivatives of 1-(2-Deoxy-4-C-hydroxymethyl-α-L-threo-Pentofuranosyl)uracil

1997 ◽  
Vol 62 (7) ◽  
pp. 1114-1127 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Jan Balzarini ◽  
Antonín Holý
Keyword(s):  
Nucleophilic Substitution ◽  
Hydrogen Chloride ◽  
Thionyl Chloride ◽  
Sodium Methoxide ◽  
Thioacetic Acid ◽  
Uracil Derivatives ◽  
Derivatives Of ◽  
Hiv 1

3'-Chloro and 3'-acetylsulfanyl derivatives of 1-(2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil were prepared by reaction of 2,3'-anhydro-1-{5'-O-benzoyl-4'-C-[(benzoyloxy)methyl]-2'-deoxy-α-L-erythro-pentofuranosyl}uracil (3) with hydrogen chloride and thioacetic acid, respectively. The reaction with hydrogen chloride gave a mixture of N-1 and N-3 substituted uracil derivatives 12 and 14. Reaction of 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-α-L-threo-pentofuranosyl}uracil (7) with thionyl chloride and subsequent debenzoylation afforded 1-(4-C-chloromethyl-2-deoxy-β-D-erythro-pentofuranosyl)uracil (19). Nucleophilic substitution with lithium thioacetate, followed by deacylation, converted 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (9) into 1-(2-deoxy-4-C-sulfanylmethyl-β-D-erythro-pentofuranosyl)uracil (21). The obtained thiols were oxidized with iodine or air to give 1,1'-[disulfandiylbis(2,3-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-3,1-diyl]di(pyrimidine-2,4-(1H,3H)-dione) (17) and 1,1'-[disulfandiylbis(2,5-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-5,1-diyl]di(pyrimidine-2,4(1H,3H)-dione) (22). Reaction of 1-{3-acetylsulfanyl-5-O-methanesulfonyl-4-C-[(benzoyloxy)methyl]-2,3-dideoxy-α-L-threo-pentofuranosyl)}uracil (24) with methanolic sodium methoxide afforded 1-(3,5-anhydro-2,3-dideoxy-4-C-hydroxymethyl-3-sulfanyl-α-L-threo-pentofuranosyl)uracil (25). The same reagent was used in the preparation of 1-(3,5-anhydro-2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil (26) from 1-{4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (8). From the series of 4'-substituted 2'-deoxyuridine derivatives, synthesized in this study, solely the 4'-chloromethyl derivative 19 and the oxetane derivative 26 exhibited an appreciable activity against HIV-1 and HIV-2.

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