Conformational studies on 1,3-dioxepans. Part II. 1,3:2,5:4,6-Tri-O- ethylidene-D-mannitol and some related compounds

T. B. Grindley, J. F. Stoddart, W. A. Szarek*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

1,3:2,5:4,6-Tri-O-ethylidene-D-mannitol and 2,5-O-ethylidene-1,3:4,6-di-O- methylene-D-mannitol exist in one stable configuration. On the basis of n.m.r. studies and the comparative stabilities of the twist-chair (TC), twist-boat (TB), and chair (C) conformations for a seven-membered ring, it is suggested that the 1,3-dioxepan rings exist predominantly in the TC form. The chemical shift data for the O-ethylidene methine and methyl protons in the 1,3-dioxan and dioxepan rings of the above-mentioned derivatives and of 1,3:4,6-di-O- ethylidene-2,5-O-methylene-D-mannitol are compared.

Original languageEnglish (US)
Pages (from-to)623-626
Number of pages4
JournalJournal of the Chemical Society B: Physical Organic
DOIs
StatePublished - Jan 1 1969

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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