Schatz J (2009)
Publication Type: Journal article, Original article
Publication year: 2009
Original Authors: Maas G., Muller A., Endres A., Schatz J.
Publisher: Elsevier
Book Volume: 65
Pages Range: 5733-5738
DOI: 10.1016/j.tet.2009.05.014
2-Acyl-1,4-bis(methoxycarbonyl)-3-[3-(methylammonio)propyl]cyclopentadienides 1 and aqueous formaldehyde can undergo a double Mannich reaction leading to the bisbetainic 2,12-diazonia-[5,5](1,3)cyclopentadienidophanes 2. The success of this macrocyclization reaction seems to depend on the length of the ω-ammonioalkyl chain and the individual acyl substituent. In the cases of ω-(methylammonio)butyl and ω-(methylammonio)pentyl chains, as well as with ω-ammoniopropyl derivatives bearing particularly electron-rich 4-methoxybenzoyl or 2-furoyl substituents, a mixture of oligomers is formed. On the other hand, DCC-assisted cyclocondensation of 1b,d (acyl=4-methoxybenzoyl and thiophene-2-carbonyl, respectively) occurs only intramolecularly, leading to the bicyclic 6-aminopentafulvenes 4b,d in good yields. © 2009 Elsevier Ltd. All rights reserved.
APA:
Schatz, J. (2009). Formation of [5.5]cyclopentadienidophanes by macrocyclization of [3-(methylammonio)propyl]cyclopentadienides under Mannich conditions. Tetrahedron, 65, 5733-5738. https://dx.doi.org/10.1016/j.tet.2009.05.014
MLA:
Schatz, Jürgen. "Formation of [5.5]cyclopentadienidophanes by macrocyclization of [3-(methylammonio)propyl]cyclopentadienides under Mannich conditions." Tetrahedron 65 (2009): 5733-5738.
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