Bifunctionalized Allenes. Part VIII. An Efficient and Varied Method for the Synthesis of 2-Sulfonylated Alka-2,3-Dienoates

Abstract

An efficient and varied method for the synthesis of 2-sulfonylated alka-2,3-dienoates by intermediate formation of allenecarboxylates, allenyl sulfones, and propargyl sulfinates using the relatively high acidity of the hydrogen atom at the allenic C-1 atom and the [2,3]-sigmatropic rearrangement is described.

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GRAPHICAL ABSTRACT

Keywords:

• 2-Sulfonylated alka-2,3-dienoates
• allenecarboxylates
• allenyl sulfones
• synthesis

Acknowledgments

Support from the Research Fund of the Konstantin Preslavsky University of Shumen (Projects Nos. RD-05-137/2011 and RD-05-247/2012) is acknowledged. Special thanks to MSc Boris Prodanov and MSc Radost Nikolova for the technical help in the chromatographical separations.