Thionyl Chloride related reagents

Various 2,5-disubstituted furans 1 have been converted into 5-acyl-3-substituted isothiazoles 2 by treatment with ethyl carbamate, thionyl chloride and pyridine. The reactive species produced by this combination of reagents may be the highly reactive thiazyl chloride, NSCl, or a related species such as its trimer (NSCPa. This mixture of reagents was reported to be much more convenient to use than (NSC1)3 and in many cases produced higher yields of isothiazole <99S757>. 

Several related 1,2,5-thiadiazolidines have been synthesized from A,A -dialkylethylenediamines by condensation with sulfur dichloride, thionyl chloride, and sulfuryl chloride. These reagents produced the thiadiazolidines 60a, n = 0, 1, and 2, respectively. A siladiazolidine was converted into 60a (n= 1) by treatment with thionyl chloride. ... 

There have been few reports of this approach to these compounds. The reaction of the alkynic alcohol HC=C—C(Me)20H with thionyl chloride and pyridine to afford (75) probably proceeds by addition of SOCI2 across the triple bond followed by cylization of the resulting hydroxysulfinyl chloride <86AKZ124>. In a related process, reaction of R C=CCH20H with a Grignard reagent, R MgX and SO2 gives (76) <82H(19)2247>. 

Further relation between the hydroxyl groups was discovered by Orekhov and his co-workers (39, 40). When platynecine was treated with a variety of reagents (sulfuric acid, thionyl chloride, phosphorus trichloride, phosphorus pentachloride, or phosphorus oxychloride), it underwent the loss of a molecule of water to form anhydroplatynecine, CgHisNO, b.p. 

Chlorocarbonylmethoxy)-4-melhylcoumarin is a reagent related to the above mentioned carbonyl azides [499]. It is prepared from 7-hydroxy-4-methylcoumarin and bromoacelic acid. The resulting carboxylic acid is transformed into the carbonyl chloride by refluxing with thionyl chloride. Derivatives (of prostaglandins and steroids) are formed in carefully dried methylene chloride containing 4-dimethylaminopyridine as catalyst. The esters formed are sufficiently stable for chromatographic separation. 

Preparation.—From Alcohols or other Halides. Factors affecting the formation of isomerically and optically pure alkyl halides from saturated aliphatic alcohols have been discussed by Hudson and co-workers. - Reactions with thionyl chloride give reduced amounts of rearrangement products if pyridine hydrochloride is added, and isomerically pure chlorides RCl from almost all alcohols ROH if HMPT or DMF is the solvent. In the latter medium (58) is a presumed intermediate, as is the case in the reaction of alcohols with Vilsmeier reagents (59, X = Cl or Br). Such species produce halides via inversion of configuration from secondary alcohols, presumably according to Scheme 24. In the related reaction of PCI3 with unhindered primary alcohols in DMF to produce alkyl... 

Sulfonamides may also be installed through the oxidative conversion of a pre-existing functional group. For example, thiols and related sulfur moieties may be oxidatively chlorinated to provide sulfonyl chlorides (Scheme 13.4). This approach can require harsh oxidants and chlorinating reagents such as thionyl chloride or aqueous chlorine and, in some cases, necessitates separate oxidation and chlorination steps. ... 

Related Reagents. A(,A(-Diitiethylformaniide N,N -Dimethylpropyleneurea Dimethyl Sulfoxide Hexam-ethylphosphoric Triamide-Thionyl Chloride Lithium Chloride-Hexamethylphosphoric Triamide l-Methyl-2-pyrrolidinone Potassium t-Butoxide-Hexamethylphosphorie Triamide Potassium Hydride-Hexamethylphosphorie Triamide Potassium Hydroxide-Hexamethylphosphoric Triamide A(,A( -Tetramethylethylenediamine. 

Related Reagents. Dimethylchloromethyleneammonium Chloride Oxalyl Chloride Phosphorus(III) Chloride Phos-phorus(V) Oxide Phosphorus Oxychloride Thionyl Chloride Triphenylphosphine-Carbon Tetrachloride Triphenylphosphine Dichloride. 

Related Reagents. Bis(trichloromethyl) Carbonate Phos-phorus(V) Oxide Phosphorus Oxychloride-Zinc(II) Chloride Thionyl Chloride p-Tolyl Vinyl Sulfoxide Trichloromethyl Chloroformate. 

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