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1. 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

Author

VERA CIRIN-NOVTA, MIRJANA POPSAVIN, LJUBICA RADIC, and VELIMIR POPSAVIN

Subjects
5-anhydro-L-idose, 5:4, 6-dianhydro-L-idose, sugar oxetanes, cycloreversion, Chemistry, QD1-999
Abstract

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.

Published
2004

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