Premium
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
Author(s) -
Butenschön Holger,
de Meijere Armin
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680620
Subject(s) - chemistry , disproportionation , trimethylenemethane , mndo , medicinal chemistry , alkali metal , delocalized electron , stereochemistry , metal , molecule , organic chemistry , catalysis , cycloaddition
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 ( 3 2− ) and some related systems as determined by semiempirical (MNDO) calculations are discussed. Thereby, 3 2− 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 3 2− by reacting tetraenes 12 with Na led to the formation of tris(dialkylamino)triquinacenes 9 , presumably by a kind of reduction/disproportionation mechanism.