Isomerism in bicyclic diacetals. Part I. 1,3:2,4- and 1,4:2,3- Di-O-methylene- erythritol

Ian J. Burden, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Acid-catalysed methylenation of erythritol affords 1,3 2,4- and 1,4:2,3-di-O-methylene-erythritol and a small amount of 1,4-anhydro-2,3-O-methylene-erythritol. Constitutional assignments have been made to the diacetals on the basis of their 1H n.m.r. and mass spectra. Deuteriation studies and the Janthanide shift reagent, Eu(fod)3, have been employed to investigate the conformational behaviour of the 1,4:2,3-diacetal in solution by 1H n.m.r. spectroscopy. Acid-catalysed equilibration of the 1,3:2,4- and 1,4:2,3-diacetals indicates that there is a free energy difference of 1·37 kcal mol-1 in favour of the former at room temperature. The significance of these results is discussed in terms of electronic effects associated with the -0-C-C-O-fragments as well as steric effects.

Original languageEnglish (US)
Pages (from-to)666-674
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
DOIs
StatePublished - 1975

ASJC Scopus subject areas

  • Chemistry(all)

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