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- Title
Synthesis of 1,2-Diols and Their Base-Initiated Rearrangement to Butyrolactones.
- Authors
Moliterno, Mauro; Margarita, Cristiana; Panarello, Silvia; Salvio, Riccardo; Bella, Marco
- Abstract
1,2-Diols 3 have been synthesized by the aldol addition of hydroxy esters 1 to propargyl aldehydes 2 in dichloromethane. These 1,2-diols undergo a base-initiated rearrangement under mild conditions in methanol with an unusual 1,2-alkyl shift to afford interesting α,β-unsaturated γ-butyrolactones 4. A possible mechanism is postulated on the basis of experimental evidence and the results of DFT calculations.
- Subjects
ALDOLS; HYDROXY esters; METHANOL; BUTYROLACTONES; DENSITY functional theory; GLYCOL synthesis
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 31, p6896
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201402853