The first example of a domino Diels-Alder/retro-Diels-Alder reaction of 1,3-dienic δ-sultones with alkynes: a simple synthesis of m-terphenyl dicarboxy derivatives from 4,6-diphenyl-[1,2]oxathiine 2,2-dioxide

Abstract

[1,1′;3′,1′′]Terphenyl-4′,5′-dicarboxylic acid derivatives were prepared from 1,3-dienic δ-sultone 4,6-diphenyl-[1,2]oxathiine 2,2-dioxide via Diels-Alder/retro-Diels-Alder reaction with dimethyl acetylenedicarboxylate under thermal, microwave or high-pressure activation.

Keywords:

• alkynes
• sultones
• Diels-Alder reaction
• m-terphenyl derivatives
• high pressure

Acknowledgements

Financial support of this work by the Deutsche Forschungsgemeinschaft and the Rosa-Luxemburg-Foundation is gratefully acknowledged.

Notes

Crystallographic data for the structure 1 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 693463.

Additional information

Notes on contributors

Olga Kataeva

X-ray diffraction analysis.