The reaction of hydroquinone and monosubstituted hydroquinones with dimethyl chloromalonate

Autor:	Stephen B. Bostock, Andrew Hunter Morris Renfrew, Christopher M. Ecob
Rok vydání:	1979
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Nucleophilic addition Hydroquinone chemistry Fragmentation (mass spectrometry) Base (chemistry) Furan Yield (chemistry) Organic chemistry Medicinal chemistry Sodium methoxide
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :2382
ISSN:	1364-5463 0300-922X
Popis:	Hydroquinone and monosubstituted hydroquinones free from –I,–M groups react with dimethyl chloromalonate in methanolic sodium methoxide solution to give 2-oxido-benzo[b]furan derivatives (1). The mechanism of this base catalysed C-alkylation is interpreted in terms of initial mono-O-alkylation followed by fragmentation and 1,4-addition of dimethyl sodiomalonate to the nascent 1,4-benzoquinone so formed. The procedure furnishes, in moderate to high yield, products which cannot be prepared readily by direct nucleophilic addition to 1,4-benzoquinones.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9e0698da9be661c6c901fba2d1a6873c https://doi.org/10.1039/p19790002382 Zobrazit plný text záznamu