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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
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
id
16703fa2-6987-414f-9924-5c2b2fd9d9d0 (old id 128422)
date added to LUP
2007-07-13 14:58:30
date last changed
2016-10-13 04:28:53
@misc{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    = {ARRAY(0xad1c580)},
  series       = {Heterocycles},
  title        = {Synthesis and X-ray analysis of isomeric diazadithia-pentacenes.},
  volume       = {60},
  year         = {2003},
}