Synthesis and structure of polyunsaturated [10]paracyclophane annulated by two azulene rings

Shigeyasu Kuroda; Yuji Obata; Nguyen Chung Thanh; Ryuta Miyatake; Yoshikazu Horino; Mitsunori Oda

doi:10.1016/j.tetlet.2007.11.067

Synthesis and structure of polyunsaturated [10]paracyclophane annulated by two azulene rings

Shigeyasu Kuroda^*, Yuji Obata, Nguyen Chung Thanh, Ryuta Miyatake, Yoshikazu Horino, Mitsunori Oda

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

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

7 Scopus citations

Abstract

The polyunsaturated [10]cyclophane 4 was synthesized from 1,4-diacetylbenzene by a four-step sequence involving the modified Yasunami azulene synthesis, introduction of two butenone units, and a subsequent McMurry coupling reaction. The crystal structures of 4 and the synthetic intermediate 8 was determined by X-ray crystallographic analysis and the results reveal that (1) the benzene ring of 4 is distorted as a boat form with relatively small bending angles and (2) the azulene rings of 8 show large out-of-plane deformation along the short azulene molecular axis.

Original language	English
Pages (from-to)	552-556
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2007.11.067
State	Published - 2008/01/14

Keywords

2H-Cyclohepta[b]fura-2-one
Azulene
Cyclophanes
McMurry coupling
X-ray crystallographic analysis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.11.067

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title = "Synthesis and structure of polyunsaturated [10]paracyclophane annulated by two azulene rings",

abstract = "The polyunsaturated [10]cyclophane 4 was synthesized from 1,4-diacetylbenzene by a four-step sequence involving the modified Yasunami azulene synthesis, introduction of two butenone units, and a subsequent McMurry coupling reaction. The crystal structures of 4 and the synthetic intermediate 8 was determined by X-ray crystallographic analysis and the results reveal that (1) the benzene ring of 4 is distorted as a boat form with relatively small bending angles and (2) the azulene rings of 8 show large out-of-plane deformation along the short azulene molecular axis.",

keywords = "2H-Cyclohepta[b]fura-2-one, Azulene, Cyclophanes, McMurry coupling, X-ray crystallographic analysis",

author = "Shigeyasu Kuroda and Yuji Obata and Thanh, {Nguyen Chung} and Ryuta Miyatake and Yoshikazu Horino and Mitsunori Oda",

year = "2008",

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day = "14",

doi = "10.1016/j.tetlet.2007.11.067",

language = "英語",

volume = "49",

pages = "552--556",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis and structure of polyunsaturated [10]paracyclophane annulated by two azulene rings

AU - Kuroda, Shigeyasu

AU - Obata, Yuji

AU - Thanh, Nguyen Chung

AU - Miyatake, Ryuta

AU - Horino, Yoshikazu

AU - Oda, Mitsunori

PY - 2008/1/14

Y1 - 2008/1/14

N2 - The polyunsaturated [10]cyclophane 4 was synthesized from 1,4-diacetylbenzene by a four-step sequence involving the modified Yasunami azulene synthesis, introduction of two butenone units, and a subsequent McMurry coupling reaction. The crystal structures of 4 and the synthetic intermediate 8 was determined by X-ray crystallographic analysis and the results reveal that (1) the benzene ring of 4 is distorted as a boat form with relatively small bending angles and (2) the azulene rings of 8 show large out-of-plane deformation along the short azulene molecular axis.

AB - The polyunsaturated [10]cyclophane 4 was synthesized from 1,4-diacetylbenzene by a four-step sequence involving the modified Yasunami azulene synthesis, introduction of two butenone units, and a subsequent McMurry coupling reaction. The crystal structures of 4 and the synthetic intermediate 8 was determined by X-ray crystallographic analysis and the results reveal that (1) the benzene ring of 4 is distorted as a boat form with relatively small bending angles and (2) the azulene rings of 8 show large out-of-plane deformation along the short azulene molecular axis.

KW - 2H-Cyclohepta[b]fura-2-one

KW - Azulene

KW - Cyclophanes

KW - McMurry coupling

KW - X-ray crystallographic analysis

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DO - 10.1016/j.tetlet.2007.11.067

M3 - 学術論文

AN - SCOPUS:37448999682

SN - 0040-4039

VL - 49

SP - 552

EP - 556

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -

Synthesis and structure of polyunsaturated [10]paracyclophane annulated by two azulene rings

Abstract

Keywords

ASJC Scopus subject areas

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