Synthesis and properties of the first Mobius annulenes

被引:103
|
作者
Ajami, Darinsh
Hess, Kirsten
Koehler, Felix
Nather, Christian
Oeckler, Oliver
Simon, Arndt
Yamamoto, Chiyo
Okamoto, Yoshio
Herges, Rainer
机构
[1] Univ Kiel, Inst Organ Chem, D-24118 Kiel, Germany
[2] Max Planck Inst Festkorperforsch, D-70569 Stuttgart, Germany
[3] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan
关键词
annulenes; aromaticity; metathesis; Mobius twist; photochemistry;
D O I
10.1002/chem.200600215
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Heilbronner in 1964 predicted that annulenes with "... a planar perimeter of N=4r AO's, which would yield an open shell configuration when occupied by 4r electrons, can be twisted into a closed shell Mobius strip perimeter without loss in it electron energy". We have been able to synthesize the first [4n]annulene with such a Mobius topology and now present further Mobius isomers and the details of their preparation as stable compounds. To address the question whether the twist in the a system has an effect on the properties we systematically investigate energy, geometry and magnetic parameters of a large number isomers of [16]annulenes. The Mobius twisted annulenes are consistently more aromatic than the non-twisted isomers. This is true for the parent as well as our benzoannelated systems. Our results are in contrast to those published recently by C. Castro, W L. Karney, P. von R. Schleyer et al.
引用
收藏
页码:5434 / 5445
页数:12
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