On the reaction of α-(2-hydroxyphenoxy)alkylketones with dimethylsulphoxonium methylide. A novel route to 2-substituted-2,3-dihydro-2-hydroxymethyl-1,4-benzodioxins

Autor:	Aldo Salimbeni, Elso Manghisi, Alberto Arnone
Rok vydání:	1988
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Nucleophile Bicyclic molecule Ylide Stereochemistry Intramolecular force Organic Chemistry Hydroxymethyl Phenols Ring (chemistry) Medicinal chemistry
Zdroj:	Journal of Heterocyclic Chemistry. 25:943-947
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570250346
Popis:	A new route to 2-substituted-2,3-dihydro-2-hydroxymethyl-1,4-benzodioxins 3 based on the reaction of α-(2-hydroxyphenoxy)alkylketones 1 with dimethylsulphoxonium methylide in dimethylsulphoxide is reported. Besides the desired compounds 3, the isomeric 2H-3,4-dihydro-1,5-benzodioxepines 4 were also isolated, generally as minor products. The concurrent formation of 3 and 4 has been interpreted as occurring through the intermediate oxiranes 2, which can undergo intramolecular nucleophilic attack at either of the carbon atoms of the epoxy ring.
Databáze:	OpenAIRE
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