In:
European Journal of Organic Chemistry, Wiley, Vol. 2006, No. 14 ( 2006-07), p. 3116-3124
Kurzfassung:
The deprotonation of N ‐allylbenzimidazolium halides 9a – d initially results in the formation of the N ‐allyldibenzotetraazafulvalenes 10 . These electron‐rich olefins rearrange to give 1,1′,2′,3′‐tetraalkyl‐1′,2′‐dihydro‐2,2′‐bibenzimidazoles 13 , either by a 3‐aza‐Cope rearrangement or by a homolytic N ‐alkyl bond cleavage and addition of the radical at the 2′‐position of the bibenzimidazole. Alternatively, double N ‐alkyl bond cleavage gives rise to 1,1′‐dialkyl‐2,2′‐bibenzimidazoles 14 . All reaction pathways were studied by use of quantum chemical calculations at the DFT/B3‐LYP/TZVP//DFT/BP86/SV(P) level, by comparison of the activation parameters for the radical and the concerted rearrangement mechanisms with the experimentally obtained products.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Materialart:
Online-Ressource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2006:14
DOI:
10.1002/ejoc.200600087
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2006
ZDB Id:
1475010-7
