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Digitale Medien

Azokupplungen an 3,4-Dimethoxyfuran (1978)

Iten, Peter Xaver ; Eugster, Conrad Hans

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 61 (1978), S. 1033-1038

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Details

ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Diazo coupling of 3,4-dimethoxyfuran with aryl diazonium ions3,4-Dimethoxyfuran (1) easily reacts with aryl diazonium chloride in aqueous pyridine in an expected 1, 4-addition reaction. From the isolable primary addition product pyridine is displaced by alcohols, phenols or thiols to yield 4-alkoxy- or 4-phenoxy- or 4-thiophenoxy-derivatives of 2,3-dimethoxy-2-buten-4-olide (3). Attempts to convert them into azo compounds by a base catalysed 1, 6-elimination reaction failed. Oxidation of 3a and 3c with DDQ results in the formation of the mono p-nitrophenylhydrazone of 3, 4-dimethoxymaleic acid anhydride. On the other hand, the thiophenoxy compound 3g is smoothly converted by MnO2 into the authentic furan-2-azobenzene derivative 5.

Zusätzliches Material: 1 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19780610313

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