Back to Search
Start Over
Synthesis of Heterocyclic [8]Circulenes and Related Structures.
- Source :
-
Synlett . 2016, Vol. 27 Issue 4, p498-525. 28p. - Publication Year :
- 2016
-
Abstract
- In this account we give an overview of the synthesis and properties of heterocyclic [8]circulenes. Much of the interest in studying heterocyclic [8]circulenes stems from the planar cyclooctatetraene core often contained in these compounds, which in principle is antiaromatic. We start with a short introduction to the hydrocarbon [n]circulenes and proceed to describe the synthetic chemistry involved in creating tetraoxa[8]circulenes, with particular focus on the acid-mediated oligomerization of benzo- or naphthoquinones, resulting in some simple rules for predicting the outcome of the oligomerization reactions. These rules have guided the synthetic strategies for the preparation of azatrioxa[8]circulenes and diazadioxa[8]circulenes, which will be described in separate sections of this account. More traditional synthetic strategies have been applied in the preparation of octathia[8]circulene, tetrathiatetraselena[8]circulene, and a number of other heterocyclic [8]circulenes, and these synthetic efforts will be highlighted. Finally, a section describing structures that are closely related to the heterocyclic [8]circulenes will be presented, and at the end we will comment on the extensive theoretical work regarding the question of aromaticity/anti-aromaticity of the central cyclooctatetraene of heterocyclic[8]circulenes. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 09365214
- Volume :
- 27
- Issue :
- 4
- Database :
- Academic Search Index
- Journal :
- Synlett
- Publication Type :
- Academic Journal
- Accession number :
- 113146476
- Full Text :
- https://doi.org/10.1055/s-0035-1560524