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σ-Bishomoconjugation (σ-Bishomoaromaticity) in 4C/3(2)e Cations-Scope and Limitations.

Authors :
Prinzbach H
Reinbold J
Bertau M
Voss T
Martin HD
Mayer B
Heinze J
Neschchadin D
Gescheidt G
Prakash GKS
Olah GA
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2001 Mar 02; Vol. 40 (5), pp. 911-914.
Publication Year :
2001

Abstract

For the seco-dodecahedradiene 1, in which the distance d <subscript>ππ</subscript> between the carbon atoms of the two double bonds ranges from 2.90 to 3.20 Å and pyramidalization angles Φ range from 14.9 to 35.5°, the geometrical prerequisites for in-plane (σ)-homoconjugative (σ-bishomoaromatic) electron delocalization in 4C/3(2)e cations could be better defined. Whilst the 4C/3e radical cation is persistent in a matrix, the 4C/2e dication in superacid medium is, at best, an intermediate en route to the stable bisallylic dication.<br /> (© 2001 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.)

Details

Language :
English
ISSN :
1521-3773
Volume :
40
Issue :
5
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
29712179
Full Text :
https://doi.org/10.1002/1521-3773(20010302)40:5<911::AID-ANIE911>3.0.CO;2-B