Construction of polycyclic systems by cyclocarbonylation. Part 3. A novel palladium-or platinum-catalyzed cyclocarbonylation reaction of cinnamyl compounds for …

H Matsuzaka, Y Hiroe, M Iwasaki, Y Ishii…

Index: Matsuzaka, Hiroyuki; Hiroe, Yoshitaka; Iwasaki, Masakazu; Ishii, Youichi; Koyasu, Yukio; Hidai, Masanobu Journal of Organic Chemistry, 1988 , vol. 53, # 16 p. 3832 - 3838

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Citation Number: 37

Abstract

Cinnamyl compounds undergo smooth cyclocarbonylation to afford 1-naphthol derivatives at 160 OC under 60 atm of CO in the presence of AczO, NEk, and a catalytic amount of palladium-or platinum-phosphine complexes. Similar cyclocarbonylation of 3-(2'-naphthyl) allyl acetate selectively proceeds to give 4-phenanthryl acetate. The mechanistic investigation reveals that cyclocarbonylation of cinnamyl compounds proceeds through ...