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Cycloaddition of 3,4-Dimethoxyfuran with 1,4-Benzoquinones under High Pressure

✍ Scribed by Janusz Jurczak; Tomasz Koz̀gluk; Marek Tkacz; Conrad Hans Eugster


Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
205 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis


High‐pressure cycloaddition of 3,4‐dimethoxyfuran with 1,4‐benzoquinone, toluquinone and 2,3‐dimethoxy‐1,4‐benzoquinone show, at 7 kbar and room temperature, prevailing formation of endo‐isomers. Raising pressure (or temperature) results in a surprising increase of the exo‐isomer. By catalytic hydrogenation of a mixture 3a/4a, followed by chromatography, the pure diastereomers 5 and 6 were obtained.


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