Studies on heterocyclic analogs of azulene. VI. Cycloadditions of styryl-substituted aza analogs of azulene with dimethyl acetylenedicarboxylate.
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概要
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8-[(<I>E</I>)-Styryl]-1-azaazulenes stereospecifically react with dimethyl acetylenedicarboxylate to form <I>trans</I>-7<I>H</I>-6a-azacyclobuta[<I>j</I>]cyclopent[<I>cd</I>]azulene (<B>3</B>), which undergoes thermal rearrangement into 3-[(<I>E</I>)-styryl]3<I>H</I>-2a-azacyclopent[<I>cd</I>]azulene and 3a,4-dihydro-3<I>H</I>-2a-azadicyclopent[<I>cd</I>, <I>ij</I>]azulene (<B>7</B>), or isomerization into 3<I>H</I>-2a-azacyclopenta[<I>ef</I>]heptalene by silica gel. Compound <B>7</B> is oxidized during the course of reaction to yield 11-oxo-2a<I>H</I>-7,10b-methano-2a-azacyclopenta[<I>ab</I>]cycloundecene, compound <B>3</B> forming 5a,6-dihydro-3<I>H</I>-2a-azadicyclopenta[<I>ef</I>, <I>kl</I>]heptalene upon reaction with acetylene. The formation of <B>3</B> could be accounted for in terms of a symmetry-allowed thermal [<SUB>π</SUB>2<SUB>s</SUB>+<SUB>π</SUB>2<SUB>a</SUB>+<SUB>π</SUB>6<SUB>a</SUB>] cycloaddition.
- 公益社団法人 日本化学会の論文
著者
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Abe Noritaka
Department Of Pure And Applied Chemistry Faculty Of Science And Technology Tokyo University Of Scien
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Nishiwaki Tarozaemon
Department of Chemistry, Faculty of Science, Yamaguchi University
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