Diazadioxa[8]circulenes: Planar Antiaromatic Cyclooctatetraenes. Issue 50 (5th November 2013)
- Record Type:
- Journal Article
- Title:
- Diazadioxa[8]circulenes: Planar Antiaromatic Cyclooctatetraenes. Issue 50 (5th November 2013)
- Main Title:
- Diazadioxa[8]circulenes: Planar Antiaromatic Cyclooctatetraenes
- Authors:
- Hensel, Thomas
Trpcevski, Denis
Lind, Christopher
Grosjean, Rémi
Hammershøj, Peter
Nielsen, Christian B.
Brock‐Nannestad, Theis
Nielsen, Bjarne E.
Schau‐Magnussen, Magnus
Minaev, Boris
Baryshnikov, Gleb V.
Pittelkow, Michael - Abstract:
- <abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>In this paper we describe a new class of antiaromatic planar cyclooctatetraenes: the diazadioxa[8]circulenes. The synthesis was achieved by means of a new acid‐mediated oxidative dimerization of 3, 6‐dihydroxycarbazoles to yield the diazadioxa[8]circulenes in high yields. The synthetic protocol appears to be general, and is a one‐pot transformation in which two CC bonds and two CO bonds are formed with the loss of two molecules of water. We also present a detailed characterization of the optical and electrochemical properties of this new class of stable planar cyclooctatetraenes. The properties of the diazadioxa[8]circulenes are compared with the properties of isoelectronic tetraoxa[8]circulenes and azatrioxa[8]circulenes. We discuss the antiaromatic nature of the planar central cyclooctatetraene moiety. The antiaromatic nature of the planar cyclooctatetraenes was studied by using computational methods (NICS calculations), and these calculations reveal that the central eight‐membered ring has antiaromatic character.</p> </abstract>
- Is Part Of:
- Chemistry. Volume 19:Issue 50(2013)
- Journal:
- Chemistry
- Issue:
- Volume 19:Issue 50(2013)
- Issue Display:
- Volume 19, Issue 50 (2013)
- Year:
- 2013
- Volume:
- 19
- Issue:
- 50
- Issue Sort Value:
- 2013-0019-0050-0000
- Page Start:
- 17097
- Page End:
- 17102
- Publication Date:
- 2013-11-05
- Subjects:
- Chemistry -- Periodicals
540 - Journal URLs:
- http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3765 ↗
http://onlinelibrary.wiley.com/ ↗ - DOI:
- 10.1002/chem.201303194 ↗
- Languages:
- English
- ISSNs:
- 0947-6539
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 3168.860500
British Library DSC - BLDSS-3PM
British Library STI - ELD Digital store - Ingest File:
- 3322.xml