ChemInform Abstract: UEBER DIE UMSETZUNG DER MUCOCHLORSAEURE MIT ALKYLMERCAPTANEN IN SAUREM MEDIUM

Bobrova, T. I.; Volodkovich, S. D.; Kukalenko, S. S.

doi:10.1002/chin.197535188

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“…Ethers 2-4 and sulfide 5 react with aromatic and aliphatic thiols similarly to the proper mucochloric acid. The 5 monosubstituted product (6) crystallizes as a racemate to give dimers usual for car boxylic acids. In the crystal of 4 monosubstituted product (8), a branched system of hydrogen bonds is formed owing to the simultaneous presence of hydroxy and carboxy groups in the molecule.…”

Section: Methodsmentioning

confidence: 99%

“…1 A large number of publications are devoted to reactions of 2(5H) furanones with N , С , О , and Р nucleophiles; however, among reactions with S nucleophiles, only those with thiols were described. [5][6][7][8][9][10][11] Our recent studies of reactions of mucochloric acid with various sulfur containing nucleophiles 11-13 were * Dedicated to Academician A. I. Konovalov on his 75th birthday. mainly aimed at elucidating the conditions for selective thiolation, preparation of sulfides of different structural types, investigation of their spatial and electronic struc tures, and the possibilities to be involved in intermole cular contacts.…”

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confidence: 99%

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Reactions of 2-mercaptoacetic acid with mucochloric acid and its derivatives

Kurbangalieva¹,

Devyatova²,

Kosolapova³

et al. 2009

Russ Chem Bull

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The stable products of reactions of mucochloric acid and some of its ethers with 2 mer captoacetic acid were synthesized and characterized. The variation of experimental conditions allowed targeted introduction of a sulfur containing fragment into particular position of the heterocycle: the reaction in aqueous potassium hydroxide gives 3 substituted 2(5H) furanone, the triethylamine additive in nonaqueous solvents facilitates the formation of 4 substituted products, and acid catalysis results in the replacement of the hydroxy (methoxy) group at С(5).(3,4 Dichloro 2 oxo 2,5 dihydrofuran 5 ylthio)ethanoic acid and (3 chloro 5 hydroxy 2 oxo 2,5 dihydrofuran 4 ylthio)ethanoic acid were characterized by X ray diffraction; their crystal and gas phase structures were discussed. The 5 monosubstituted product crystallizes as a racemate, while 4 monosubstituted product, as a conglomerate.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%