Synthesis of 2,3-Dihydrobenzo[1,4]dithiin-Fused Porphyrins

Abstract

This article describes the preparation of (ethylenedithio)bicyclo[2.2.2]octadiene-fused porphyrins 13 and 14a,b as soluble precursors of 2,3-dihydrobenzo[1,4]dithiin-fused porphyrins and the retro Diels–Alder conversion of the precursors 13 and 14a,b.

Keywords:

• Benzo[1,4]dithiin
• benzoporphyrin
• retro Diels–Alder reaction
• ring expansion reaction of 1,3-dithiolane

Acknowledgments

Dedicated to Professor Naomichi Furukawa on the occasion of his 70th birthday.

This work was partially supported by the Sasagawa Scientific Research Grant from The Japan Science Society (G.J.). We used ethyl isocyanoacetate from the Nippon Synthetic Chem. Ind. (Osaka Japan).