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1H-and 13C-NMR Investigation of Pentafulvenes

✍ Scribed by Peter Bönzli; Albin Otter; Markus Neuenschwander; Hanspeter Huber; Hans Peter Kellerhals

Publisher
John Wiley and Sons
Year
1986
Tongue
German
Weight
686 KB
Volume
69
Category
Article
ISSN
0018-019X

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✦ Synopsis

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'Hand 13C-NMR spectra of a series of 6-(p-X-phenyl)pentafulvenes 1-9 as well as of 6-R-substituted and 6,6-R',R2-disubstituted pentafulvenes 1&23 have been analysed. It turns out that the n-system of pentafulvenes is an attractive probe for the investigation ofelectronic substituent effects. Changes of uicinal H,H-coupling consfanis with increasing electron-donating capacity of the substituents X and R are interpreted in terms of an increasing x delocalisation in the 5-membered ring, and linear correlations of Hammett substituent constants 0: or MNDO-calculated C-C bond lengths and 3J values are observed. On the other hand, a systematic high-field shift of "C chemical shifis of the ring C-atoms is induced by electron-releasing substituents R and X, which decreases in the series C(5) > C(2)/C(3) > C(I)/C(4), and which mainly reflects changes in n-charge density.

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