Studien zum Ablauf der Substitution VIII Organische Sulfohalogenide als Pseudohalogene

Abstract

Z . Elektlo-*) Hieriiber soll an aiiderer Stelle berichtet werden. chem. 57, i 3 (1953).

New synthesis and anti-HIV and antiviral properties of 3-arylsulfonyl derivatives of 4-ydroxycoumarin and 4-hydroxyquinolone

“…Diethyl (toluene-4-sulfonyl)malonate 5a was prepared by reaction of ethylchloroformate and (toluene-4-sulfonyl)methylmagnesium bromide with a 22% yield [37], diethyl phenylsulfonylmalonate 5c by the reaction of benzenesulfonic anhydride with diethyl ethoxy-magnesium malonate with 46% yield [38], and diethyl phenylsulfonyl malonate by the reaction of benzenesulfonic anhydride with diethyl sodiomalonate with 24% yield [39]. In order to improve the yields of the desired esters, two other possible routes were investigated.…”

Benzenesulfonyl chloride does react with tertiary amines. The Hinsberg test in proper prospective

“…Volume 49, Number More recently Horner and Nickel (7) took up the problem and reported a superior laboratory technique for preparing II along with experiments describing its properties. They found:…”

“…II + CH2(C02Et)2 -* C6H5SOl!CH(COsEt)2 + (CHANHCl" (6) VII (4) A mixture of thiophenol and II affords trimethylamine hydrochloride, diphenyldisulfidc, VIII, and diphenyldisulfone, IX (eqn. (7)) instead of phenyl bcnzenethiosulfonate, X (eqn. (8)).…”

“…More recently Horner and Nickel (7) identified the major products of reaction of I and XI in ether-water in the yields indicated (eqn. ( 11)).…”

Reaction of bromonaphthalene with potassium tert-butoxide and tert-butyl alcohol in dimethyl sulfoxide

“…At that time no ¿erí-butyl 1-naphthyl ether was found and a mixture of 1-and 2-naphthols was the major product. 6 We now would like to report on the reaction of 1-and 2-bromonaphthalene with potassium ¿erí-butoxide in a ¿erí-butyl alcohol-DMSO solvent mixture. This reaction not only gave ¿eríbutyl 1-and 2-naphthyl ethers and naphthols but also eleven other identifiable products (see Scheme I).…”