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

TitleConformational studies on 1,3-dioxepans. Part II. 1,3:2,5:4,6-Tri-O- ethylidene-D-mannitol and some related compounds
Authors
Grindley, T. B.Stoddart, J. F.Szarek, W. A.
Issue Date1969
Citation
Journal of the Chemical Society B: Physical Organic, 1969, p. 623-626 How to Cite?
DOI: http://dx.doi.org/10.1039/j29690000623
Abstract1,3:2,5:4,6-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.
Persistent Identifierhttp://hdl.handle.net/10722/332821
ISSN
0045-6470

 

DC FieldValueLanguage
dc.contributor.authorGrindley, T. B.-
dc.contributor.authorStoddart, J. F.-
dc.contributor.authorSzarek, W. A.-
dc.date.accessioned2023-10-06T05:14:32Z-
dc.date.available2023-10-06T05:14:32Z-
dc.date.issued1969-
dc.identifier.citationJournal of the Chemical Society B: Physical Organic, 1969, p. 623-626-
dc.identifier.issn0045-6470-
dc.identifier.urihttp://hdl.handle.net/10722/332821-
dc.description.abstract1,3:2,5:4,6-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.-
dc.languageeng-
dc.relation.ispartofJournal of the Chemical Society B: Physical Organic-
dc.titleConformational studies on 1,3-dioxepans. Part II. 1,3:2,5:4,6-Tri-O- ethylidene-D-mannitol and some related compounds-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/j29690000623-
dc.identifier.scopuseid_2-s2.0-37049136559-
dc.identifier.spage623-
dc.identifier.epage626-

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