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

Article abstract of DOI:10.1080/00397919108016422

The synthetic usefulness of 'acrylic' tin compounds has been largely demonstrated by BALDWIN and coworkers. 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.

Full text of DOI:10.1080/00397919108016422

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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
D. Colombani a , C. Navarro a , M. Degueil-Castaing a
& B. Maillard a
a Laboratoire de Chimie Organique et
Organométallique, associé au CNRS (URA 35),
Université Bordeaux I, F-33405, TALENCE-CEDEX,
FRANCE
Version of record first published: 24 Sep 2006.
To cite this article: D. Colombani, C. Navarro, M. Degueil-Castaing & B. Maillard
(1991): 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,
Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 21:14, 1481-1487
To link to this article: http://dx.doi.org/10.1080/00397919108016422
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