Synthese von Pentafulvalen durch oxidative Kupplung von Cyclopentadienid mittels Kupfer(II)-chlorid
Publication type: Journal Article
Publication date: 1986-10-29
scimago Q2
wos Q3
SJR: 0.491
CiteScore: 3.0
Impact factor: 1.8
ISSN: 0018019X, 15222675
Catalysis
Organic Chemistry
Drug Discovery
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Synthesis of Pentafulvalene by Oxidative Coupling of Cyclopentadienide with Copper(II) Chloride
Starting with a nearly quantitative coupling of cyclononatetraenide 7 to 1, 1′-dihydrononafulvalene 8 by means of AgBF4, a simple general synthetic concept for fulvalenes is outlined (Scheme 2), consisting in an oxidative coupling of ‘Huckel anions’ like 2 and 7 to 1, 1′-dihydrofulvalenes 10 with Ag(I) or Cu(II) salts, followed by deprotonation (11) and oxidation (12); it has been realised in the case of pentafulvalene (1; overall yield 61%; Scheme 3) and 1,2:5,6-dibenzopentafulvalene (18; overall yield 66%, Scheme 4). NMR-spectroscopic investigations show that 1 is a non-aromatic compound with strongly alternating bond-lengths, its π-system being even more localised than that of simple pentafulvenes. In fact, 1 is extremely reactive in concentrated solutions above −50°. Besides of polymerisations, Diels-Alder dimerisation 119 followed by a rearrangement 1920 takes place (Scheme 5).
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Escher A., Rutsch W., Neuenschwander M. Synthese von Pentafulvalen durch oxidative Kupplung von Cyclopentadienid mittels Kupfer(II)-chlorid // Helvetica Chimica Acta. 1986. Vol. 69. No. 7. pp. 1644-1654.
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Escher A., Rutsch W., Neuenschwander M. Synthese von Pentafulvalen durch oxidative Kupplung von Cyclopentadienid mittels Kupfer(II)-chlorid // Helvetica Chimica Acta. 1986. Vol. 69. No. 7. pp. 1644-1654.
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RIS
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TY - JOUR
DO - 10.1002/hlca.19860690719
UR - https://doi.org/10.1002/hlca.19860690719
TI - Synthese von Pentafulvalen durch oxidative Kupplung von Cyclopentadienid mittels Kupfer(II)-chlorid
T2 - Helvetica Chimica Acta
AU - Escher, Andr
AU - Rutsch, Werner
AU - Neuenschwander, Markus
PY - 1986
DA - 1986/10/29
PB - Wiley
SP - 1644-1654
IS - 7
VL - 69
SN - 0018-019X
SN - 1522-2675
ER -
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BibTex (up to 50 authors)
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@article{1986_Escher,
author = {Andr Escher and Werner Rutsch and Markus Neuenschwander},
title = {Synthese von Pentafulvalen durch oxidative Kupplung von Cyclopentadienid mittels Kupfer(II)-chlorid},
journal = {Helvetica Chimica Acta},
year = {1986},
volume = {69},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/hlca.19860690719},
number = {7},
pages = {1644--1654},
doi = {10.1002/hlca.19860690719}
}
Cite this
MLA
Copy
Escher, Andr, et al. “Synthese von Pentafulvalen durch oxidative Kupplung von Cyclopentadienid mittels Kupfer(II)-chlorid.” Helvetica Chimica Acta, vol. 69, no. 7, Oct. 1986, pp. 1644-1654. https://doi.org/10.1002/hlca.19860690719.