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Synthesis and stability of 1,1-tetramethylene- and 1,1-pentamethylene-1H-azulenium ions

โœ Scribed by Mitsunori Oda; Aya Sakamoto; Takuya Uchiyama; Takanori Kajioka; Ryuta Miyatake; Shigeyasu Kuroda

Book ID
104261365
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
134 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Direct cycloalkylation of 1,6-dihydroazulene and subsequent hydride abstraction with trityl salt gave the title cations 3 and 4. These cations showed greater kinetic stability than the three-and four-membered ring homologs, and their pKR+ values indicated greater thermodynamic stability compared with the known disubstituted tropylium cations.

๐Ÿ“œ SIMILAR VOLUMES

Synthesis and reactions of 1,1-trimethyl
Synthesis and reactions of 1,1-trimethylene-1H-azulenium ion
โœ Mitsunori Oda; Aya Sakamoto; Ryuta Miyatake; Shigeyasu Kuroda ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 227 KB

Direct cyclobutylation of 1,6-dihydroazulene gave the spiro hydrocarbon 6, which was subjected to hydride abstraction to lead to the title cation 4. Its hexafluorophosphate salt was isolated as crystals. The cation 4 showed distinctive chemical behavior compared with its thrce-membcrcd ring homolog.