Unexpected cycloreversion of a tosylated sugar oxetane under E2 conditions. The facile formation of 2-(2-furanyl)-1,3-dioxolane from a novel 2,5:4,6-dianhydro-L-idose derivative

Autor:	VERA CIRIN-NOVTA, MIRJANA POPSAVIN, LJUBICA RADIC, VELIMIR POPSAVIN
Jazyk:	angličtina
Rok vydání:	2004
Předmět:	5-anhydro-L-idose 5:4 6-dianhydro-L-idose sugar oxetanes cycloreversion Chemistry QD1-999
Zdroj:	Journal of the Serbian Chemical Society, Vol 69, Iss 2, Pp 117-122 (2004)
Druh dokumentu:	article
ISSN:	0352-5139
Popis:	2,5:4,6-Dianhydro-3-O-p-toluenesulfonyl-L-idose ethylene acetal (4) was synthesized with the aim of studying its chemical behaviour in the presence of several basic agents (Bu4NF/MeCN, NaOMe/MeOH, KOBut/ButOH/THF, and NaH/DMSO). Treatment of 4 with sodium hydride in dimethyl sulphoxide at room temperature unexpectedly gave the 2-(2-furanyl)-1,3-dioxolane. The mechanism of the process presumably involved the initial conversion of 4 to the corresponding 2,3-unsaturated derivative 5, followed by a facile oxetane ring cycloreversion by the elimination of formaldehyde.
Databáze:	Directory of Open Access Journals
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