Details
| Original language | English |
|---|---|
| Pages (from-to) | 1658-1669 |
| Number of pages | 12 |
| Journal | Helvetica chimica acta |
| Volume | 68 |
| Issue number | 6 |
| Publication status | Published - 25 Sept 1985 |
| Externally published | Yes |
Abstract
The synthesis and characterization of the novel 4,7‐bis(dialkylamino)tricyclo[5.2.1.04,10]deca‐1(10), 2,5,8‐tetraenes 12 from 1,4,7‐trihalotriquinacenes 8 and secondary amines is reported. The structural and electronic characteristics of these as well as the acepentalene dianion (32−) and some related systems as determined by semiempirical (MNDO) calculations are discussed. Thereby, 32− should be a triply etheno‐bridged trimethylenemethane dianion exhibiting Y‐delocalization favored over the formation of a peripheral 10π‐electronic system. Attempts directed towards the generation of 32− by reacting tetraenes 12 with Na led to the formation of tris(dialkylamino)triquinacenes 9, presumably by a kind of reduction/disproportionation mechanism.
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
- Chemistry(all)
- Inorganic Chemistry
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In: Helvetica chimica acta, Vol. 68, No. 6, 25.09.1985, p. 1658-1669.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The Synthesis of 4,7‐Bis(dialkylamino)tricyclo[5.2.1.04,10]deca‐1(10),2,5,8‐tetraenes and their Reduction with Alkali Metal
AU - Butenschön, Holger
AU - de Meijere, Armin
PY - 1985/9/25
Y1 - 1985/9/25
N2 - The synthesis and characterization of the novel 4,7‐bis(dialkylamino)tricyclo[5.2.1.04,10]deca‐1(10), 2,5,8‐tetraenes 12 from 1,4,7‐trihalotriquinacenes 8 and secondary amines is reported. The structural and electronic characteristics of these as well as the acepentalene dianion (32−) and some related systems as determined by semiempirical (MNDO) calculations are discussed. Thereby, 32− should be a triply etheno‐bridged trimethylenemethane dianion exhibiting Y‐delocalization favored over the formation of a peripheral 10π‐electronic system. Attempts directed towards the generation of 32− by reacting tetraenes 12 with Na led to the formation of tris(dialkylamino)triquinacenes 9, presumably by a kind of reduction/disproportionation mechanism.
AB - The synthesis and characterization of the novel 4,7‐bis(dialkylamino)tricyclo[5.2.1.04,10]deca‐1(10), 2,5,8‐tetraenes 12 from 1,4,7‐trihalotriquinacenes 8 and secondary amines is reported. The structural and electronic characteristics of these as well as the acepentalene dianion (32−) and some related systems as determined by semiempirical (MNDO) calculations are discussed. Thereby, 32− should be a triply etheno‐bridged trimethylenemethane dianion exhibiting Y‐delocalization favored over the formation of a peripheral 10π‐electronic system. Attempts directed towards the generation of 32− by reacting tetraenes 12 with Na led to the formation of tris(dialkylamino)triquinacenes 9, presumably by a kind of reduction/disproportionation mechanism.
UR - http://www.scopus.com/inward/record.url?scp=18944387937&partnerID=8YFLogxK
U2 - 10.1002/hlca.19850680620
DO - 10.1002/hlca.19850680620
M3 - Article
AN - SCOPUS:18944387937
VL - 68
SP - 1658
EP - 1669
JO - Helvetica chimica acta
JF - Helvetica chimica acta
SN - 0018-019X
IS - 6
ER -