TRIS(3,6-DI-T-BUTYL-1-AZULENYL)METHYL CATION - HYDROCARBON CATION WITH THE HIGHEST PK(R)(+) VALUE

Authors
ITO S MORITA N ASAO T
Citation
S. Ito et al., TRIS(3,6-DI-T-BUTYL-1-AZULENYL)METHYL CATION - HYDROCARBON CATION WITH THE HIGHEST PK(R)(+) VALUE, Tetrahedron letters, 35(5), 1994, pp. 751-754
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
5
Year of publication
1994
Pages
751 - 754
Database
ISI
SICI code
0040-4039(1994)35:5<751:TC-HCW>2.0.ZU;2-D
Abstract
Tris(3,6-di-t-butyl-1-azulenyl)methyl (5), tri(3-t-butyl-1-azulenyl)me thyl (10), and tri(6-t-butyl-1-azulenyl)methyl (11) hexafluorophosphat es were synthesized. Their pK(R)(+) values were determined as 14.3, 13 .2, and 13.7, respectively, and the value of 5 showed the highest one as carbocation ever reported. The extreme stability of methyl cation 5 is mainly attributable to steric effects of six bulky I-butyl groups in addition to the contribution of dipolar structure of three azulene rings.