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Rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions of triacetylenic 15-membered aza macrocycles: A comparative structural study

A variety of new nitrogen-containing 15-membered triacetylenic macrocycles with one or two alkyl substituents in a propargylic position have been efficiently synthesized and completely characterized. These macrocyclic systems undergo [2 + 2 + 2] cycloaddition reactions, leading to the corresponding fused tetracycles with a benzene core on treatment with Wilkinson’s catalyst, [RhCl(PPh 3) 3]. The effects of alkyl chains have been evaluated on both the efficiency of the reaction and the conformational and structural analysis of the reactants

We would like to thank the Spanish MICINN (projects CTQ2008-05409 and CTQ2011-23121), and the Generalitat de Catalunya (project 2009SGR637) for their financial support. S.B. thanks the University of Girona (UdG) for a predoctoral fellowship. Spectroscopic data have been partially funded by the University of Girona under the project with reference STR-CT00059

© Organometallics, 2012, vol. 31, núm.1, p. 318-326

American Chemical Society (ACS)

Author: Brun Massó, Sandra
Torrent i Palomeras, Anna
Pla i Quintana, Anna
Roglans i Ribas, Anna
Fontrodona, Xavier
Benet Buchholz, Jordi
Parella Coll, Teodor
Date: 2012 January 9
Abstract: A variety of new nitrogen-containing 15-membered triacetylenic macrocycles with one or two alkyl substituents in a propargylic position have been efficiently synthesized and completely characterized. These macrocyclic systems undergo [2 + 2 + 2] cycloaddition reactions, leading to the corresponding fused tetracycles with a benzene core on treatment with Wilkinson’s catalyst, [RhCl(PPh 3) 3]. The effects of alkyl chains have been evaluated on both the efficiency of the reaction and the conformational and structural analysis of the reactants
We would like to thank the Spanish MICINN (projects CTQ2008-05409 and CTQ2011-23121), and the Generalitat de Catalunya (project 2009SGR637) for their financial support. S.B. thanks the University of Girona (UdG) for a predoctoral fellowship. Spectroscopic data have been partially funded by the University of Girona under the project with reference STR-CT00059
Format: application/pdf
ISSN: 0276-7333 (versió paper)
1520-6041 (versió electrònica)
Document access: http://hdl.handle.net/10256/11344
Language: eng
Publisher: American Chemical Society (ACS)
Collection: MICINN/PN 2012-2014/CTQ2011-23121
MEC/PN 2009-2011/CTQ2008-05409-C02-02
AGAUR/2009-2014/2009 SGR-637
Reproducció digital del document publicat a: http://dx.doi.org/10.1021/om200927f
Articles publicats (D-Q)
Is part of: © Organometallics, 2012, vol. 31, núm.1, p. 318-326
Rights: Tots els drets reservats
Subject: Reaccions d’addició
Addition reactions
Rodi
Rhodium
Catalitzadors de rodi
Rhodium catalyst
Ciclització (Química)
Ring formation (Chemistry)
Title: Rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions of triacetylenic 15-membered aza macrocycles: A comparative structural study
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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