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Synlett 1995; 1995(4): 375-377
DOI: 10.1055/s-1995-4971
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Diels-Alder Reactions of 3-Bromo-1,5-azulenequinone and 3-Bromo-1,7-azulenoequinone with Several Dienophiles. High-Pressure Acceleration

Tetsuo Nozoe1 , Hitoshi Takeshita2 , Yong Zhe Yan, Akira Mori
  • 1Tokyo Research Laboratories, Kao Corporations, Ltd, Bunka, Sumida-ku, Tokyo 131
  • 2Institute of Advanced Material Study, 86, Kyushu University, Kasuga-koen, Kasuga, Fukuoka 816
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Publication History

Publication Date:
31 December 2000 (online)

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Upon heating under high-pressure conditions (300 MPa), 3-bromo-1,5- and 3-bromo-1,7-azulenequinones regioselectively afforded the Diels-Alder adducts with several dienophiles in good yields. Except for styrene and acrylonitrile, pronounced endo-selectivity was observed for the formation of the products. In the case of cyclopentadiene, stereo- and regioselective [4+2] process occurred in refluxing benzene.

Diels-Alder reaction - high-pressure - Condensed dihydrohomobarrelenones

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