The reactions of 4-hydroxymethylsydnones with alcohols and benzene

Autor:	Hsien-Ju Tien, Shaw-Tao Lin, Gwo-Ming Fang, Ling-Ling Tien
Rok vydání:	1993
Předmět:	chemistry.chemical_compound Electrophilic substitution Chemistry Organic Chemistry Kinetics General Chemistry Lewis acids and bases Methylation Primary alcohol Benzene Medicinal chemistry Catalysis
Zdroj:	Canadian Journal of Chemistry. 71:796-800
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v93-105
Popis:	In the presence of a Lewis acid, 4-hydroxymethylsydnones undergo reaction with alcohols and benzene to form 4-alkoxysydnones 1a, bis(4-sydnonylmethyl) ethers 1b, or 4-benzylsydnones 1d depending upon the reaction conditions. At 0 °C, compounds 1a and 1b are formed from compound 1 in benzene and alkyl alcohol, respectively. Compound 1b is converted to compound 1d at 40 °C. When the reactions are carried out in a cosolvent of benzene and methyl alcohol at 40 °C, compound 1a is obtained preferentially and followed by conversion to compound 1d. The α-sydnonyl-methylene cation derived from either compound 1 or 1a is responsible for the formation of compound 1d.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2d412a83b805f1908e3dc29f5c366122 https://doi.org/10.1139/v93-105 Zobrazit plný text záznamu