Furan-2, 3-diones as masked dipoles: synthesis of isotetronic acids and mechanistic considerations. Issue 36 (8th September 2016)
- Record Type:
- Journal Article
- Title:
- Furan-2, 3-diones as masked dipoles: synthesis of isotetronic acids and mechanistic considerations. Issue 36 (8th September 2016)
- Main Title:
- Furan-2, 3-diones as masked dipoles: synthesis of isotetronic acids and mechanistic considerations
- Authors:
- Barbier, Vincent
Couty, François
David, Olivier R.P. - Abstract:
- Abstract: The formal dipolar behaviour of furan-2, 3-diones is illustrated by their reaction with ethyl glyoxylate under Lewis basic activation uniquely, giving access to isotetronic derivatives. The Janus-type nature of the activated species, both nucleophilic and electrophilic is revealed by ring-opening of the starting ketolactone. An unexpected reversible side-reaction was identified by in situ monitoring. Graphical abstract:
- Is Part Of:
- Tetrahedron. Volume 72:Issue 36(2016)
- Journal:
- Tetrahedron
- Issue:
- Volume 72:Issue 36(2016)
- Issue Display:
- Volume 72, Issue 36 (2016)
- Year:
- 2016
- Volume:
- 72
- Issue:
- 36
- Issue Sort Value:
- 2016-0072-0036-0000
- Page Start:
- 5646
- Page End:
- 5651
- Publication Date:
- 2016-09-08
- Subjects:
- Organocatalysis -- Lewis base -- Heterocyclic chemistry -- Physical organic chemistry -- Dipole
Chemistry, Organic -- Periodicals
547.005 - Journal URLs:
- http://www.elsevier.com/journals ↗
- DOI:
- 10.1016/j.tet.2016.07.072 ↗
- Languages:
- English
- ISSNs:
- 0040-4020
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 8796.850000
British Library DSC - BLDSS-3PM
British Library STI - ELD Digital store - Ingest File:
- 475.xml