Synthesis of (3-Ethoxycarbonyl But-3-en-2-yl)phenyl Sulfone and (2-Ethoxycarbonyl But-2-en-1-yl)phenyl Sulfone from Ethyl 2-Bromomethyl But-2-enoate
- 1 July 1991
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 21 (14) , 1481-1487
- https://doi.org/10.1080/00397919108016422
Abstract
The synthetic usefullness of “acrylic” tin compounds has been largely demonstrated by BALDWIN and coworkers1. We wanted to apply this methodology to prepare the peroxide precursors. Thus, we needed to synthesize (2-ethoxycarbonyl prop-2-enyl) phenyl sulfone 1, (2-ethoxycarbonyl but-2-en-1-yl) phenyl sulfone 2 and (3-ethoxycarbonyl but-3-en-2-yl) phenyl sulfone 3. We wish to report the synthesis of such compounds using the advantage of the complexing effect of Polyethyleneoxide 400 (PEO 400) on alkali cations. We also must to report the isomerisation of 2 to 3 in presence of traces of sodium sulfinate which make access to 2 difficult.Keywords
This publication has 11 references indexed in Scilit:
- A new general synthesis of sulfones from alkyl or aryl halides and p-toluenesulfonhydrazideTetrahedron, 1989
- Synthetic potential of the tertiary-amine-catalysed reaction of activated vinyl carbanions with aldehydesTetrahedron, 1988
- Organic Syntheses without Solvent: Preparation of Sulfones and DithioacetalsSynthesis, 1987
- Radical reactions in synthesis: carbon–carbon bond formation from 2-substituted allyl trialkyl stannanesJournal of the Chemical Society, Chemical Communications, 1986
- Synthesis of sulfones by phase-transfer alkylation of arenesulfinate saltsThe Journal of Organic Chemistry, 1985
- Necic acid synthons. Part 2. Regioselectivity in the reactions of Z-2-bromomethyl-2-alkenoate esters with selected carbon nucleophilesJournal of the Chemical Society, Perkin Transactions 1, 1982
- Wittig-Horner Reaction in Heterogeneous Media; 1. An Easy Synthesis of Ethyl α-Hydroxymethylacrylate and Ethyl α-Halomethylacrylates using Formaldehyde in WaterSynthesis, 1982
- Convenient Alternative Synthesis of Sulfones in Aprotic Medium using Phase-Transfer CatalysisSynthesis, 1979
- Polymer Supported Reagents. The Use of Anion Exchange Resins in the Synthesis of SulfonesSynthesis, 1979
- An Improved Synthesis of Sulfones using Tetrabutyl-ammonium SulfinatesSynthesis, 1975