Consecutive HDDA and TDDA reactions of silicon-tethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity.

Akihito Mitake,Natsuhiko Sugimura,Rikako Nagai,Ayato Sekine,Takanori Shibata,Hideaki Takano,Kyalo Stephen Kanyiva

doi:10.1039/c9sc00960d

Akihito Mitake, Natsuhiko Sugimura + Show 5 more

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https://doi.org/10.1039/c9sc00960d

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Abstract

Silicon-tethered tetraynes possessing a 1,3-diyne moiety underwent consecutive hexadehydro- and tetradehydro-Diels-Alder reactions to give a series of fused polycyclic aromatic compounds containing a dibenzosilole skeleton. The benzene ring in the product acted as a 1,3-diene and reacted with the active alkyne as well as oxygen to provide [4 + 2] cycloadducts.

Highlights

All publication charges for this article have been paid for by the Royal Society of Chemistry
Silicon-tethered tetraynes possessing a 1,3-diyne moiety underwent consecutive hexadehydro- and tetradehydro-Diels–Alder reactions to give a series of fused polycyclic aromatic compounds containing a dibenzosilole skeleton
The intramolecular TDDA reaction of arylalkynes, where part of the arene acts as an ene moiety, is attractive, because fused polycyclic aromatic compounds can be prepared in one pot

Summary

Introduction

All publication charges for this article have been paid for by the Royal Society of Chemistry. Consecutive HDDA and TDDA reactions of silicontethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity†

Results

Conclusion