Chemical and Pharmaceutical Bulletin p. 1298 - 1304 (1996)
Update date:2022-09-26
Topics:
Saithoh, Toshiaki
Oyama, Taichi
Horiguchi, Yoshie
Toda, Jun
Sano, Takehiro
Thermal reaction of aroylketenes 2 with cyclic enol ethers such as 2,3- dihydrofuran (A), 2,3-dihydropyran (B), 1-trimethylsilyloxycyclopentene (C), 1-trimethylsilyloxycyclohexene (D), 3-trimethylsilyloxyindene (E), and 4- trimethylsilyloxy-1,2-dihydronaphalene (F) was carried out to investigate the reactivity of 2 with these olefins. The main reaction was Michael-type addition to give the 1,3-diketones 3 and 9, and the 1,3,5-triketones 13, 15, 18, and 20, depending on the olefins used. The addition of the olefins was facilitated by introduction of a nitro or chloro group into the aryl part of 2 and was profoundly retarded by steric hindrance of the olefins.
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