Synthesis and properties of 1,6-methano[10]annuleno[3,4-c]thiophene and its 1,3-dicyano derivative

Shigeyasu Kuroda; Mitsunori Oda; Mizuho Nagai; Yuko Wada; Ryuta Miyatake; Tatsuki Fukuda; Hiroaki Takamatsu; Nguyen Chung Thanh; Masaru Mouri; Yanmei Zhang; Mayumi Kyogoku

doi:10.1016/j.tetlet.2005.08.145

Synthesis and properties of 1,6-methano[10]annuleno[3,4-c]thiophene and its 1,3-dicyano derivative

Shigeyasu Kuroda^*, Mitsunori Oda, Mizuho Nagai, Yuko Wada, Ryuta Miyatake, Tatsuki Fukuda, Hiroaki Takamatsu, Nguyen Chung Thanh, Masaru Mouri, Yanmei Zhang, Mayumi Kyogoku

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

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

8 Scopus citations

Abstract

New thiophene-annulated 1,6-methano[10]annulene 1 and 2 were synthesized. The anisotropic deshielding effect from the π-electron system, based on the chemical shift values of the bridged methylene protons, is reduced compared with that of 3, and their crystal structures show clear bond alternation.

Original language	English
Pages (from-to)	7311-7314
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2005.08.145
State	Published - 2005/10/24

Keywords

1,6-Methano[10]annulene
Ring current
Thiophene
X-ray crystallographic analysis
o-Quinodimethane

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{5907e9c3a35a4ea1a2e2fe7654b2208f,

title = "Synthesis and properties of 1,6-methano[10]annuleno[3,4-c]thiophene and its 1,3-dicyano derivative",

abstract = "New thiophene-annulated 1,6-methano[10]annulene 1 and 2 were synthesized. The anisotropic deshielding effect from the π-electron system, based on the chemical shift values of the bridged methylene protons, is reduced compared with that of 3, and their crystal structures show clear bond alternation.",

keywords = "1,6-Methano[10]annulene, Ring current, Thiophene, X-ray crystallographic analysis, o-Quinodimethane",

author = "Shigeyasu Kuroda and Mitsunori Oda and Mizuho Nagai and Yuko Wada and Ryuta Miyatake and Tatsuki Fukuda and Hiroaki Takamatsu and Thanh, {Nguyen Chung} and Masaru Mouri and Yanmei Zhang and Mayumi Kyogoku",

year = "2005",

month = oct,

day = "24",

doi = "10.1016/j.tetlet.2005.08.145",

language = "英語",

volume = "46",

pages = "7311--7314",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "43",

}

TY - JOUR

T1 - Synthesis and properties of 1,6-methano[10]annuleno[3,4-c]thiophene and its 1,3-dicyano derivative

AU - Kuroda, Shigeyasu

AU - Oda, Mitsunori

AU - Nagai, Mizuho

AU - Wada, Yuko

AU - Miyatake, Ryuta

AU - Fukuda, Tatsuki

AU - Takamatsu, Hiroaki

AU - Thanh, Nguyen Chung

AU - Mouri, Masaru

AU - Zhang, Yanmei

AU - Kyogoku, Mayumi

PY - 2005/10/24

Y1 - 2005/10/24

N2 - New thiophene-annulated 1,6-methano[10]annulene 1 and 2 were synthesized. The anisotropic deshielding effect from the π-electron system, based on the chemical shift values of the bridged methylene protons, is reduced compared with that of 3, and their crystal structures show clear bond alternation.

AB - New thiophene-annulated 1,6-methano[10]annulene 1 and 2 were synthesized. The anisotropic deshielding effect from the π-electron system, based on the chemical shift values of the bridged methylene protons, is reduced compared with that of 3, and their crystal structures show clear bond alternation.

KW - 1,6-Methano[10]annulene

KW - Ring current

KW - Thiophene

KW - X-ray crystallographic analysis

KW - o-Quinodimethane

UR - http://www.scopus.com/inward/record.url?scp=25444531460&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2005.08.145

DO - 10.1016/j.tetlet.2005.08.145

M3 - 学術論文

AN - SCOPUS:25444531460

SN - 0040-4039

VL - 46

SP - 7311

EP - 7314

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Synthesis and properties of 1,6-methano[10]annuleno[3,4-c]thiophene and its 1,3-dicyano derivative

Abstract

Keywords

ASJC Scopus subject areas

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