Some transformations of acetylenic alcohol epoxides

Autor:	M. P. Khmel, N. N. Baranov, M. S. Malinovskii
Rok vydání:	1977
Předmět:	chemistry.chemical_classification Organic Chemistry Epoxide Alcohol Sulfuric acid Triple bond Ring (chemistry) Chloride Medicinal chemistry chemistry.chemical_compound chemistry Furan medicine Organic chemistry Alkyl medicine.drug
Zdroj:	Chemistry of Heterocyclic Compounds. 13:934-937
ISSN:	1573-8353 0009-3122
DOI:	10.1007/bf00472440
Popis:	It is shown that the hydration of acetylenic alcohol epoxides containing an epoxide ring in the β position relative to the triple bond in the presence of sulfuric acid leads to the formation of acetylenic triols: 6-methyl-4-heptyne-1,2,6-, 7-methyl-5-octyne-2,3,7-, 2,7-dimethyl-5-octyne-2,3,7-, and 2,3,7-trimethyl-5-octyne-2,3,7-triols. It was established that the hydration process is hampered as the number of alkyl substituents attached to the epoxide ring increases. The triols were subjected to intramolecular cyclization under the influence of mercuric chloride to the corresponding chloromercurated derivatives of furan: 2-(1-chloromercuri-2-methyl-1-propenyl) and 5-methyi-2-(1-chloromercuri-2-methyl-1-propenyl)furans. The IR and PMR spectral data are presented.
Databáze:	OpenAIRE
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