Reaction of benzil with methylsulfinylcarbanion. II. Reaction mechanism

Trisler, John C.; Doty, James K.; Robinson, J. Michael

doi:10.1021/jo01263a045

Cited by 11 publications

(5 citation statements)

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“…“APH” has been successfully reacted with 2-aroyl- 347 , and 3-aroyl furans 349 and delivers the corresponding deacylated furanes 348 and 350 as well as the related benzoic acids in good yield and with extremely high regiocontrol (Scheme ). In those cases, the nature of the substituants attached to the aryl group part of the aroyl moiety as well as the solvent used do not seem to play a crucial role in both yields and regiocontrols (compare Scheme to Scheme , entry b).…”

Section: “Anhydrous Potassium Hydroxide” In Organic Synthesismentioning

confidence: 99%

Synthesis of Alkali Metal Carboxylates and Carboxylic Acids Using “Wet” and “Anhydrous” Alkali Metal Hydroxides

Krief

Kremer

2010

Chem. Rev.

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Section: “Anhydrous Potassium Hydroxide” In Organic Synthesismentioning

confidence: 99%

Synthesis of Alkali Metal Carboxylates and Carboxylic Acids Using “Wet” and “Anhydrous” Alkali Metal Hydroxides

Krief

Kremer

2010

Chem. Rev.

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“…Multisubstituted furans are of great importance because numerous interesting compounds bearing such a heterocyclic ring exhibit a wide array of activity and are also building blocks for organic synthesis. , Many synthetic routes toward furan rings with specific substitution patterns have been designed and well applied, , such as direct functionalization of furan rings, cyclocondensation of 1,4-dicarbonyl compounds (Paal−Knorr synthesis), Feist−Bénary synthesis, and transition metal-catalyzed cycloisomerization of alkynyl or allenyl substrates. , To our surprise, of these developed strategies, − there are few literature reports for the syntheses of tetrasubstituted furans with three aryl groups and a ketone, an ester, or a cyano group . Therefore, a strong demand remains to develop an efficient approach.…”

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confidence: 99%

Preparation of Tetrasubstituted Furans via Intramolecular Wittig Reactions with Phosphorus Ylides as Intermediates

et al. 2010

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Novel preparation of tetrasubstituted furans, starting from the Michael acceptors, tributylphosphine, and acyl chlorides, is realized. A broad range of highly functional furans can be efficiently generated in one step at room temperature within 10 min to 21 h in moderate to high yields (60-99%). The reaction was proposed to proceed via intramolecular Wittig-type reactions, using phosphorus ylides as intermediates.

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“…3-Carbethoxy-4-(2',2'-dichlorovinyl)-2,5-hexanedione (7).-Sodium (0.9 g, 0.039 g-atom) was dissolved in 13 ml of absolute ethanol. Ethyl acetoacetate (4.9 g, 0.038 mol) was added to this solution.…”

Section: Methodsmentioning

confidence: 99%

“…Wave numbei; cm-1 Scheme II 2-amino-4-methyl-4-hydroxy-5-(2',2'-dichlorovinyl)thiazoline hydrochloride (6) with thiourea and 3-carbethoxy-4-(2 ',2' -dichlorovinyl) -2,5 -hexanedione (7) with ethyl sodioacetoacetate, whereas the reaction of 2a with triethylamine (8) in ether solution resulted in the formation of 1,3,3-trichloro-l-propenyl methyl ketone (10a) in 62% yield.…”

Section: C12c=ch-ch-cochsmentioning

confidence: 99%