Bulletin of the Chemical Society of Japan p. 616 - 619 (1995)
Update date:2022-08-17
Topics:
Kiji
Okano
Kitamura
Yokoyama
Kubota
Kurita
2,6,6-Trimethyl-5-(2,5-dimethyl-3-furyl and -3-thienyl)-3-heptyn-2,5-diols were carbonylated in benzene in the presence of 1:1 - Pd(OAc)2/I2 as the catalyst. The reaction at 90°C under 80 atm of carbon monoxide for 5 h directly gave both E and Z isomers of t-butyl-substituted furyl- or thienyl fulgides. The former had been reported impossible to synthesize by the Stobbe condensation. Similarly, furyl- and thienylfulgides with an isopropyl group were synthesized by this method. The fulgides were isolated by column chromatography in 37-75% yields. Coloring quantum yields of t-butyl-furyl- and -thienylfulgides are 0.79 and 0.73, respectively, which are the greatest in each series of fulgides with the same heteroaromatic ring.
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