Synthesis of 1,6′-Bi- and 1,6′:3,6″-terazulenes from 1-pyridyl- and 1,3-Di(pyridyl)azulenes by the Ziegler-Hafner method

Taku Shoji; Atsuyo Yamamoto; Erika Shimomura; Mitsuhisa Maruyama; Shunji Ito; Tetsuo Okujima; Kozo Toyota; Noboru Morita

doi:10.1246/cl.130157

Synthesis of 1,6′-Bi- and 1,6′:3,6″-terazulenes from 1-pyridyl- and 1,3-Di(pyridyl)azulenes by the Ziegler-Hafner method

Taku Shoji, Atsuyo Yamamoto, Erika Shimomura, Mitsuhisa Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota, Noboru Morita

SCI - Chemistry

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

11 Citations (Scopus)

Abstract

The synthesis of 1,6′-biazulenes 3a and 3b and 1,6′:3,6″- terazulenes 7a and 7b was established by one-pot reactions via the Zincke-type ring-opening of the corresponding pyridinium salts with diethylamine, followed by the reaction with cyclopentadiene in the presence of sodium methoxide. The intramolecular charge-transfer characters between azulene rings were investigated by UVvis spectroscopy and theoretical calculations.

Original language	English
Pages (from-to)	638-640
Number of pages	3
Journal	Chemistry Letters
Volume	42
Issue number	6
DOIs	https://doi.org/10.1246/cl.130157
Publication status	Published - 2013

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1246/cl.130157

Cite this

@article{47a94676cf5f405892efd01d23614f3e,

title = "Synthesis of 1,6′-Bi- and 1,6′:3,6″-terazulenes from 1-pyridyl- and 1,3-Di(pyridyl)azulenes by the Ziegler-Hafner method",

abstract = "The synthesis of 1,6′-biazulenes 3a and 3b and 1,6′:3,6″- terazulenes 7a and 7b was established by one-pot reactions via the Zincke-type ring-opening of the corresponding pyridinium salts with diethylamine, followed by the reaction with cyclopentadiene in the presence of sodium methoxide. The intramolecular charge-transfer characters between azulene rings were investigated by UVvis spectroscopy and theoretical calculations.",

author = "Taku Shoji and Atsuyo Yamamoto and Erika Shimomura and Mitsuhisa Maruyama and Shunji Ito and Tetsuo Okujima and Kozo Toyota and Noboru Morita",

year = "2013",

doi = "10.1246/cl.130157",

language = "English",

volume = "42",

pages = "638--640",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "6",

}

TY - JOUR

T1 - Synthesis of 1,6′-Bi- and 1,6′:3,6″-terazulenes from 1-pyridyl- and 1,3-Di(pyridyl)azulenes by the Ziegler-Hafner method

AU - Shoji, Taku

AU - Yamamoto, Atsuyo

AU - Shimomura, Erika

AU - Maruyama, Mitsuhisa

AU - Ito, Shunji

AU - Okujima, Tetsuo

AU - Toyota, Kozo

AU - Morita, Noboru

PY - 2013

Y1 - 2013

N2 - The synthesis of 1,6′-biazulenes 3a and 3b and 1,6′:3,6″- terazulenes 7a and 7b was established by one-pot reactions via the Zincke-type ring-opening of the corresponding pyridinium salts with diethylamine, followed by the reaction with cyclopentadiene in the presence of sodium methoxide. The intramolecular charge-transfer characters between azulene rings were investigated by UVvis spectroscopy and theoretical calculations.

AB - The synthesis of 1,6′-biazulenes 3a and 3b and 1,6′:3,6″- terazulenes 7a and 7b was established by one-pot reactions via the Zincke-type ring-opening of the corresponding pyridinium salts with diethylamine, followed by the reaction with cyclopentadiene in the presence of sodium methoxide. The intramolecular charge-transfer characters between azulene rings were investigated by UVvis spectroscopy and theoretical calculations.

UR - http://www.scopus.com/inward/record.url?scp=84878715076&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84878715076&partnerID=8YFLogxK

U2 - 10.1246/cl.130157

DO - 10.1246/cl.130157

M3 - Article

AN - SCOPUS:84878715076

SN - 0366-7022

VL - 42

SP - 638

EP - 640

JO - Chemistry Letters

JF - Chemistry Letters

IS - 6

ER -

Synthesis of 1,6′-Bi- and 1,6′:3,6″-terazulenes from 1-pyridyl- and 1,3-Di(pyridyl)azulenes by the Ziegler-Hafner method

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this