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Synthesis and X-ray analysis of isomeric diazadithia-pentacenes.

Nowak, M ; Pluta, K ; Kloc, C and Siegrist, Theo LU (2003) In Heterocycles 60(9). p.2045-2056
Abstract
The isomeric diazadithiapentacenes (3) and (4) were obtained in reactions of 2-chloro-3-bromoquinoline (5) with selected sulfur reagents in various conditions. The 1,4-dithiin ring opening in diazadithiapentacene (3) led to 2,3’-diquinolinyl sulfide or (via the Smiles rearrangement stage of the S→S type) to 3,3’-diquinolinyl sulfide or to diazadithiapentacene (4) depending on reaction conditions. The X-Ray study of pentacenes (3) and (4) revealed non-planar and folded structures along the central sulfur-sulfur axis. The central six-membered ring is in a boat conformation.
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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Heterocycles
volume
60
issue
9
pages
2045 - 2056
publisher
Japan Institute of Heterocyclic Chemistry
external identifiers
  • scopus:0042738000
ISSN
0385-5414
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Polymer and Materials Chemistry (LTH) (011001041)
id
16703fa2-6987-414f-9924-5c2b2fd9d9d0 (old id 128422)
date added to LUP
2016-04-04 09:20:57
date last changed
2022-01-29 17:27:40
@article{16703fa2-6987-414f-9924-5c2b2fd9d9d0,
  abstract     = {{The isomeric diazadithiapentacenes (3) and (4) were obtained in reactions of 2-chloro-3-bromoquinoline (5) with selected sulfur reagents in various conditions. The 1,4-dithiin ring opening in diazadithiapentacene (3) led to 2,3’-diquinolinyl sulfide or (via the Smiles rearrangement stage of the S→S type) to 3,3’-diquinolinyl sulfide or to diazadithiapentacene (4) depending on reaction conditions. The X-Ray study of pentacenes (3) and (4) revealed non-planar and folded structures along the central sulfur-sulfur axis. The central six-membered ring is in a boat conformation.}},
  author       = {{Nowak, M and Pluta, K and Kloc, C and Siegrist, Theo}},
  issn         = {{0385-5414}},
  language     = {{eng}},
  number       = {{9}},
  pages        = {{2045--2056}},
  publisher    = {{Japan Institute of Heterocyclic Chemistry}},
  series       = {{Heterocycles}},
  title        = {{Synthesis and X-ray analysis of isomeric diazadithia-pentacenes.}},
  volume       = {{60}},
  year         = {{2003}},
}