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Transition metal-diene complexes in organic synthesis, part 27. synthesis and reactivity of 4a,9a-dihydro-9H-carbazoles

✍ Scribed by Hans-Joachim Knölker; Gerhard Baum; Jörn-Bernd Pannek


Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
1018 KB
Volume
52
Category
Article
ISSN
0040-4020

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Transition metal complexes in organic sy
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Aryl-substituted tricarbonyl(rl4-cyclohexa -1,3-diene)iron complexes are oxidatively cyclized in protic medium in the air to tricarbonyliron-complexed 4a,9a-dihydro-9H-carbazoles. The method is applied to the total synthesis of mukonine and mukonidine.

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Transition-Metal Complexes in Organic Synthesis. Part 36. Cyclization of Tricarbonyliron Complexes by Oxygen to 4a,9a-Dihydro-9Hcarbazoles: Application to the Synthesis of Mukonine, Mukonidine, and Pyrido(3,2,1-jk)carbazoles. -A novel method for the cyclization of aryl-substituted iron complexes su

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Evidence for the structure of 13 was provided by the sharp s at 12.67 ppm (phenol OH) in the 'H-NMR spectrum. The substitution pattern was confirmed by NOE difference spectra. Irradiation at the Me signal at 2.28 ppm resulted in a NOE of the aromatic proton at 6.67 ppm.