Synthesis and thermal rearrangement of homobarrelenones. Preparation of dimethyl 1-oxo-cis-3a,7a-dihydroindene-3a,7a-dicarboxylates.
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概要
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The Diels-Alder reaction of five derivatives of 2-methoxytropone with dimethyl acetylenedicarboxylate proceeds regiospecifically giving dimethyl 1-methoxy-2-oxobicyclo[3.2.2]nona-3,6,8-triene-6,7-dicarboxylates, except in the case of 5-isopropyl-2-methoxytropone. The adducts undergo rearrangement selectively to dimethyl 7-methoxy-1-oxo-<I>cis</I>-3a,7a-dihydroindene-3a,7a-dicarboxylates, upon heating under reflux in xylene. Regiochemical aspects of the cycloaddition and mechanistic aspects of the rearrangement are discussed.
- 公益社団法人 日本化学会の論文
著者
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Uyehara Tadao
Department Of Applied Chemistry Faculty Of Engineering Utsunomiya University
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Kitahara Yoshio
Department Of Chemistry Faculty Of Science Tohoku University
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Miyakoshi Shoichi
Department of Chemistry, Faculty of Science, Tohoku University
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