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

Mitsunori Oda; Aya Sakamoto; Takuya Uchiyama; Takanori Kajioka; Ryuta Miyatake; Shigeyasu Kuroda

doi:10.1016/S0040-4039(99)00581-X

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

Mitsunori Oda^*, Aya Sakamoto, Takuya Uchiyama, Takanori Kajioka, Ryuta Miyatake, Shigeyasu Kuroda

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

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 pK(R)+ values indicated greater thermodynamic stability compared with the known disubstituted tropylium cations.

Original language	English
Pages (from-to)	3595-3596
Number of pages	2
Journal	Tetrahedron Letters
Volume	40
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4039(99)00581-X
State	Published - 1999/04/30

Keywords

Azulenium ions
Carbocations
Spiro compounds
Tropylium ions

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00581-X

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

abstract = "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 pK(R)+ values indicated greater thermodynamic stability compared with the known disubstituted tropylium cations.",

keywords = "Azulenium ions, Carbocations, Spiro compounds, Tropylium ions",

author = "Mitsunori Oda and Aya Sakamoto and Takuya Uchiyama and Takanori Kajioka and Ryuta Miyatake and Shigeyasu Kuroda",

year = "1999",

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doi = "10.1016/S0040-4039(99)00581-X",

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TY - JOUR

T1 - Synthesis and stability of 1,1-tetramethylene- and 1,1-pentamethylene- 1H-azulenium ions

AU - Oda, Mitsunori

AU - Sakamoto, Aya

AU - Uchiyama, Takuya

AU - Kajioka, Takanori

AU - Miyatake, Ryuta

AU - Kuroda, Shigeyasu

PY - 1999/4/30

Y1 - 1999/4/30

N2 - 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 pK(R)+ values indicated greater thermodynamic stability compared with the known disubstituted tropylium cations.

AB - 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 pK(R)+ values indicated greater thermodynamic stability compared with the known disubstituted tropylium cations.

KW - Azulenium ions

KW - Carbocations

KW - Spiro compounds

KW - Tropylium ions

UR - http://www.scopus.com/inward/record.url?scp=0033617154&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)00581-X

DO - 10.1016/S0040-4039(99)00581-X

M3 - 学術論文

AN - SCOPUS:0033617154

SN - 0040-4039

VL - 40

SP - 3595

EP - 3596

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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