Dispiro[cyclohexane-1,1′-(1′,7′- dihydrocyclopenta[f]azulenium)-7′,1′′-cyclohexane] perchlorate, a new highly stable hydrocarbon cation

Mitsunori Oda; Hitoshi Kainuma; Ryuta Miyatake; Shigeyasu Kuroda

doi:10.1016/S0040-4039(02)00604-4

Dispiro[cyclohexane-1,1′-(1′,7′- dihydrocyclopenta[f]azulenium)-7′,1′′-cyclohexane] perchlorate, a new highly stable hydrocarbon cation

Mitsunori Oda^*, Hitoshi Kainuma, Ryuta Miyatake, Shigeyasu Kuroda

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

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

9 Scopus citations

Abstract

The title cation was synthesized from 1,6-diacetylcyclohepta-1,3,5-triene by a six-step sequence involving an aldol reaction, the Nazarov cyclization, the Shapiro reaction and hydride abstraction, and its pK_R+ value was found to be 13.2, providing a new access to highly stable hydrocarbon cations.

Original language	English
Pages (from-to)	3485-3488
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4039(02)00604-4
State	Published - 2002/05/06

Keywords

Azulenes
Carbenium ions
Cyclohexanes
Spiro compounds
X-ray crystal structures

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(02)00604-4

Cite this

@article{e7f460a1471e487eb7f2e33aaacccfee,

title = "Dispiro[cyclohexane-1,1′-(1′,7′- dihydrocyclopenta[f]azulenium)-7′,1′′-cyclohexane] perchlorate, a new highly stable hydrocarbon cation",

abstract = "The title cation was synthesized from 1,6-diacetylcyclohepta-1,3,5-triene by a six-step sequence involving an aldol reaction, the Nazarov cyclization, the Shapiro reaction and hydride abstraction, and its pKR+ value was found to be 13.2, providing a new access to highly stable hydrocarbon cations.",

keywords = "Azulenes, Carbenium ions, Cyclohexanes, Spiro compounds, X-ray crystal structures",

author = "Mitsunori Oda and Hitoshi Kainuma and Ryuta Miyatake and Shigeyasu Kuroda",

note = "Funding Information: The present work is supported by the Grant-in-Aid for Scientific Research (No. 13640528) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. We also thank Mr. Takuya Uchiyama at Toyama University for the hybrid density functional calculations of the cation 4 .",

year = "2002",

month = may,

day = "6",

doi = "10.1016/S0040-4039(02)00604-4",

language = "英語",

volume = "43",

pages = "3485--3488",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "19",

}

TY - JOUR

T1 - Dispiro[cyclohexane-1,1′-(1′,7′- dihydrocyclopenta[f]azulenium)-7′,1′′-cyclohexane] perchlorate, a new highly stable hydrocarbon cation

AU - Oda, Mitsunori

AU - Kainuma, Hitoshi

AU - Miyatake, Ryuta

AU - Kuroda, Shigeyasu

N1 - Funding Information: The present work is supported by the Grant-in-Aid for Scientific Research (No. 13640528) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. We also thank Mr. Takuya Uchiyama at Toyama University for the hybrid density functional calculations of the cation 4 .

PY - 2002/5/6

Y1 - 2002/5/6

N2 - The title cation was synthesized from 1,6-diacetylcyclohepta-1,3,5-triene by a six-step sequence involving an aldol reaction, the Nazarov cyclization, the Shapiro reaction and hydride abstraction, and its pKR+ value was found to be 13.2, providing a new access to highly stable hydrocarbon cations.

AB - The title cation was synthesized from 1,6-diacetylcyclohepta-1,3,5-triene by a six-step sequence involving an aldol reaction, the Nazarov cyclization, the Shapiro reaction and hydride abstraction, and its pKR+ value was found to be 13.2, providing a new access to highly stable hydrocarbon cations.

KW - Azulenes

KW - Carbenium ions

KW - Cyclohexanes

KW - Spiro compounds

KW - X-ray crystal structures

UR - http://www.scopus.com/inward/record.url?scp=0037029777&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(02)00604-4

DO - 10.1016/S0040-4039(02)00604-4

M3 - 学術論文

AN - SCOPUS:0037029777

SN - 0040-4039

VL - 43

SP - 3485

EP - 3488

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Dispiro[cyclohexane-1,1′-(1′,7′- dihydrocyclopenta[f]azulenium)-7′,1′′-cyclohexane] perchlorate, a new highly stable hydrocarbon cation

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this