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σ‐Bishomoconjugation (σ‐Bishomoaromaticity) in 4C/3(2)e Cations—Scope and Limitations
Author(s) -
Prinzbach Horst,
Reinbold Jens,
Bertau Martin,
Voss Torsten,
Martin HansDieter,
Mayer Bernhard,
Heinze Jürgen,
Neschchadin Dmytro,
Gescheidt Georg,
Prakash G. K. Surya,
Olah George A.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010302)40:5<911::aid-anie911>3.0.co;2-b
Subject(s) - dication , scope (computer science) , delocalized electron , superacid , chemistry , carbon fibers , radical ion , range (aeronautics) , crystallography , computational chemistry , computer science , ion , materials science , organic chemistry , catalysis , algorithm , composite number , composite material , programming language
For the seco‐dodecahedradiene 1 , in which the distance d ππ 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.