The Synthesis of 4,7‐Bis(dialkylamino)tricyclo[5.2.1.0^4,10]deca‐1(10),2,5,8‐tetraenes and their Reduction with Alkali Metal

authored by

Holger Butenschön, Armin de Meijere

Abstract

The synthesis and characterization of the novel 4,7‐bis(dialkylamino)tricyclo[5.2.1.0^4,10]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.

External Organisation(s)

Universität Hamburg

Type

Article

Journal

Helvetica chimica acta

Volume

68

Pages

1658-1669

No. of pages

12

ISSN

0018-019X

Publication date

25.09.1985

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Catalysis, Biochemistry, Drug Discovery, Physical and Theoretical Chemistry, Organic Chemistry, Inorganic Chemistry

Electronic version(s)

https://doi.org/10.1002/hlca.19850680620 (Access: Unknown)