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Reaktionen vinyloger Oxycarbene mit Methanol (1991)

Hömberger, Günter ; Kirmse, Wolfgang ; Lelgemann, Rudolf

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1867-1869

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Details

ISSN: 0009-2940

Schlagwort(e): Carbenes, nucleophilic ; Cyclohexadienylidenes ; Pyrylium ions ; Carboxonium ions ; Chemistry ; Inorganic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Reactions of Vinylogous Oxycarbenes with MethanolThe carbenes 16 and 30 were generated in methanol/sodium methoxide by photolyses of 2-methylchromone tosylhydrazone (14) and 3,5-dimethoxy-4,4-dimethyl-2,5-cyclohexadienone tosylhydrazone (28), respectively. Neither 16 nor 30 accept methanol at the carbenic site to give products of a formal O - H insertion. Carbene 16 affords 2-methoxy-2-methyl-2H-1-benzopyran (19) by way of the benzopyrylium ion 17. The same ether was obtained from the independently prepared perchlorate of 17. Protonation of 30 was followed by demethylation of the delocalized carboxonium ion 31 to give 5-methoxy-6,6-dimethyl-2,4-cyclohexadienone (33) as the only product.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/cber.19911240826

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