File Download
There are no files associated with this item.
Links for fulltext
(May Require Subscription)
- Publisher Website: 10.1039/p19750000675
- Scopus: eid_2-s2.0-37049136441
- WOS: WOS:A1975AC41400016
- Find via
Supplementary
- Citations:
- Appears in Collections:
Article: Isomerism in bicyclic diacetals. Part II. Bicyclic methylene diacetals in the galacto, arabino, and ribo series
Title | Isomerism in bicyclic diacetals. Part II. Bicyclic methylene diacetals in the galacto, arabino, and ribo series |
---|---|
Authors | |
Issue Date | 1975 |
Citation | Journal of the Chemical Society, Perkin Transactions 1, 1975, n. 7, p. 675-682 How to Cite? |
Abstract | Studies of the acid-catalysed methylenation of tetritols with the galacto, arabino, and ribo configurations have led to the following observations: (i) dimethyl galactarate affords dimethyl 2,3:4,5- and 2,5:3,4-di-O-methylene- galactarate, (ii) methyl-D-arabinonate affords methyl 2,3:4,5-, 2,4:3,5-, and 2,5:3,4-di-O-methylene-D-arabinonate, and (iii) methyl D-ribonate affords methyl 2,4:3,5- and 2,5:3,4-di-O-methylene-D-ribonate. Vicinal coupling constant data obtained by 1H n.m.r. spectroscopy show that dimethyl 2,5:3,4-di-O-methylenegalactarate and methyl 2,5:3,4-di-O-arabinonate exist predominantly in gauche, gauche conformations in solution whereas the gauche, anti conformation is highly populated in solutions of methyl 2,5:3,4-di-O-methylene-D-ribonate. The relative stabilities of the constitutional isomers are discussed in terms of electronic effects associated with gauche oxygen-oxygen interactions in O-C||-C ||-O fragments as well as in terms of steric effects. There is no strong evidence to support the view that such gauche oxygen - oxygen interactions are an important stabilising feature in cis-fused 3,5,8,10-tetraoxabicyclo[5.3.0]decanes. |
Persistent Identifier | http://hdl.handle.net/10722/332820 |
ISSN | |
ISI Accession Number ID |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Burden, Ian J. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:14:32Z | - |
dc.date.available | 2023-10-06T05:14:32Z | - |
dc.date.issued | 1975 | - |
dc.identifier.citation | Journal of the Chemical Society, Perkin Transactions 1, 1975, n. 7, p. 675-682 | - |
dc.identifier.issn | 1472-7781 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332820 | - |
dc.description.abstract | Studies of the acid-catalysed methylenation of tetritols with the galacto, arabino, and ribo configurations have led to the following observations: (i) dimethyl galactarate affords dimethyl 2,3:4,5- and 2,5:3,4-di-O-methylene- galactarate, (ii) methyl-D-arabinonate affords methyl 2,3:4,5-, 2,4:3,5-, and 2,5:3,4-di-O-methylene-D-arabinonate, and (iii) methyl D-ribonate affords methyl 2,4:3,5- and 2,5:3,4-di-O-methylene-D-ribonate. Vicinal coupling constant data obtained by 1H n.m.r. spectroscopy show that dimethyl 2,5:3,4-di-O-methylenegalactarate and methyl 2,5:3,4-di-O-arabinonate exist predominantly in gauche, gauche conformations in solution whereas the gauche, anti conformation is highly populated in solutions of methyl 2,5:3,4-di-O-methylene-D-ribonate. The relative stabilities of the constitutional isomers are discussed in terms of electronic effects associated with gauche oxygen-oxygen interactions in O-C||-C ||-O fragments as well as in terms of steric effects. There is no strong evidence to support the view that such gauche oxygen - oxygen interactions are an important stabilising feature in cis-fused 3,5,8,10-tetraoxabicyclo[5.3.0]decanes. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the Chemical Society, Perkin Transactions 1 | - |
dc.title | Isomerism in bicyclic diacetals. Part II. Bicyclic methylene diacetals in the galacto, arabino, and ribo series | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1039/p19750000675 | - |
dc.identifier.scopus | eid_2-s2.0-37049136441 | - |
dc.identifier.issue | 7 | - |
dc.identifier.spage | 675 | - |
dc.identifier.epage | 682 | - |
dc.identifier.isi | WOS:A1975AC41400016 | - |