Novel Preparation of 1-and 3-Substituted Bicyclo [3.2. 2] nona-3, 6, 8-trien-2-ones from Tropones and 2, 3-Bis (methoxycarbonyl)-7-oxabicyclo [2.2. 1] heptadiene by …

GR Tian, S Sugiyama, A Mori, H Takeshita

Index: Tian; Sugiyama; Mori; Takeshita Bulletin of the Chemical Society of Japan, 1988 , vol. 61, # 7 p. 2393 - 2399

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Citation Number: 18

Abstract

The Diels–Alder adduct of tropone with 2, 3-bis (methoxycarbonyl)-7-oxabicyclo [2.2. 1] hepta-2, 5-diene formed homobarrelenone on heating at 130° C. Similarly prepared were 1- hydroxy-, 3-methoxy-, 1-chloro-, and 3-chlorohomobarrelenones. High-pressure cycloaddition improved the yields of the Diels–Alder adducts. In reactions of 2-methoxy-and 2-chlorotropones with the 7-oxanorbornadiene derivative, the endo-isomers were ...