𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Double aromaticity: aromaticity in orthogonal planes. The 3,5-dehydrophenyl cation.

✍ Scribed by Jayaraman Chandrasekhar; Eluvathingal D. Jemmis; Paul von Ragué Schleyer

Book ID
104246500
Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
233 KB
Volume
20
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The D3h 3,5-dehydrophenyl cation (I), which may represent the structure of Cz3+ ions observed mass spectroscopically, illustrates double aromaticity: two different aromatic systems in orthogonal planes. Cyclic conjugated polyenes with 4n+2 electrons are aromatic. 1 A large number of such systems are known. On the other hand, the presence of two mutually orthogonal Hiickel frameworks within a single molecule is unusual. Delocalization in orthogonal planes has been suggested in cyclic phosphonitrilic halides 2 and in (SNjx systems. 3 It was also predicted in cyclododeca-1,5,9-triene-3,7,11-tri-

📜 SIMILAR VOLUMES