1979
DOI: 10.1246/cl.1979.597
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Elektronenreiche Heptafulvene Als Bausteine Von Azulenen. 8-Methoxyheptafulven

Abstract: 8-Methoxyheptafulvene (5), the first C-8 monosubstituted electron-rich heptafulvene is synthesized from 1,3,5-cycloheptatriene-7-carbaldehyde dimethyl acetal (4) and lithium diisopropylamide. (8+2) π cycloadditions of (5) are described. Dimethyl azulene-1,2-dicarboxylate (9) and dimethyl 3-methoxyazulene-1,2-dicarboxylate (8) are obtained from the cycloadduct of (5) and dimethyl acetylenedicarboxylate.

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Cited by 11 publications
(2 citation statements)
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“…-Heptafulvenes 3a [42], 3b [21], 3c [43],3d [ a ] , 3e [45], 3f [2], 3g [2], 3h [2], 3i (411, 3j [2]. 3k [2], 31 NMR Spectra.…”
Section: Experimental Partmentioning
confidence: 99%
“…-Heptafulvenes 3a [42], 3b [21], 3c [43],3d [ a ] , 3e [45], 3f [2], 3g [2], 3h [2], 3i (411, 3j [2]. 3k [2], 31 NMR Spectra.…”
Section: Experimental Partmentioning
confidence: 99%
“…The transient formation of norcaradiene facilitates the ring opening of the bicyclo trienone, which forms azulene after dehydration. Using another approach, the [8+2]-cycloaddition reaction was carried out between heptafulvene and dimethyl acetylene dicarboxylate 15 . However, this reaction is impractical given the difficulties associated with obtaining the starting materials, specifically heptafulvene is very unstable 16 .…”
Section: Introductionmentioning
confidence: 99%