Facile and Efficient Synthesis of Substituted 1,4‐Dithiafulvalenes from β‐Dicarbonyl Compounds

Abstract

A facile and efficient synthetic route to substituted 1,4‐dithiafulvalenes has been developed. The precursors 2 may be easily prepared from the reactions of β‐dicarbonyl compounds 1 with CS₂ and 1,2,3‐tribromopropane under mild conditions. The elimination of HBr of 2 in basic media furnishes corresponding acetyl substituted 1,4‐dithiafulvalenes 3 in 85–93% yields. The aldol condensation reaction of 2 with various arylaldehydes affords alkenoyl substituted 1,4‐dithiofulvalenes 4 in high to excellent yields.

Keywords:

• aldol condensation
• β‐dicarbonyl compounds
• 1,4‐dithiafulvalene derivatives
• rearrangement of a double bond
• synthesis

Acknowledgment

This research was supported by the Key Grant Project of Chinese Ministry of Education (10412), the National Natural Sciences Foundation of China (20272008), and Science Foundation for Young Teachers of Northeast Normal University (20060313).