Synthesis and conformation of 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes

Ryuta Miyatake; Shigeyasu Kuroda; Takanori Kajioka; Akihide Taketani; Mitsunori Oda

doi:10.1016/S0040-4020(02)00353-8

Synthesis and conformation of 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes

Ryuta Miyatake, Shigeyasu Kuroda^*, Takanori Kajioka, Akihide Taketani, Mitsunori Oda

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

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

3 Scopus citations

Abstract

First two derivatives of 4,9-methanothia[11]annulene, 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes (4 and 5), were synthesized from the diketosulfide 6. Spectroscopic properties and X-ray crystallographic analyses revealed that 4 exists as an anti-conformer in respect of stereochemical relationship between the methano bridge and the sulfur atom both in solid state and in solution, while 5 exists as a syn-conformer in similarity to the parent of 4,9-methanothia[11]annulene (3).

Original language	English
Pages (from-to)	3647-3654
Number of pages	8
Journal	Tetrahedron
Volume	58
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4020(02)00353-8
State	Published - 2002/05/06

Keywords

Annulenes
Conformation
Density functional calculation
Heterocycles
X-ray crystal structures

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(02)00353-8

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@article{1273ada41e8d4d299acc3791006132af,

title = "Synthesis and conformation of 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes",

abstract = "First two derivatives of 4,9-methanothia[11]annulene, 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes (4 and 5), were synthesized from the diketosulfide 6. Spectroscopic properties and X-ray crystallographic analyses revealed that 4 exists as an anti-conformer in respect of stereochemical relationship between the methano bridge and the sulfur atom both in solid state and in solution, while 5 exists as a syn-conformer in similarity to the parent of 4,9-methanothia[11]annulene (3).",

keywords = "Annulenes, Conformation, Density functional calculation, Heterocycles, X-ray crystal structures",

author = "Ryuta Miyatake and Shigeyasu Kuroda and Takanori Kajioka and Akihide Taketani and Mitsunori Oda",

note = "Funding Information: This work was supported financially by a Grant-in-Aid Scientific Research (No. 10640513 to S. K. and No. 13640528 to M. O.) from the Ministry of Education, Science, Culture and Sports, Japan. We thank Dr Shengli Zuo and Mr Shinji Furuta at Toyama University for their technical assistance for the preparation of compounds 4 – 6 .",

year = "2002",

month = may,

day = "6",

doi = "10.1016/S0040-4020(02)00353-8",

language = "英語",

volume = "58",

pages = "3647--3654",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "19",

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TY - JOUR

T1 - Synthesis and conformation of 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes

AU - Miyatake, Ryuta

AU - Kuroda, Shigeyasu

AU - Kajioka, Takanori

AU - Taketani, Akihide

AU - Oda, Mitsunori

N1 - Funding Information: This work was supported financially by a Grant-in-Aid Scientific Research (No. 10640513 to S. K. and No. 13640528 to M. O.) from the Ministry of Education, Science, Culture and Sports, Japan. We thank Dr Shengli Zuo and Mr Shinji Furuta at Toyama University for their technical assistance for the preparation of compounds 4 – 6 .

PY - 2002/5/6

Y1 - 2002/5/6

N2 - First two derivatives of 4,9-methanothia[11]annulene, 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes (4 and 5), were synthesized from the diketosulfide 6. Spectroscopic properties and X-ray crystallographic analyses revealed that 4 exists as an anti-conformer in respect of stereochemical relationship between the methano bridge and the sulfur atom both in solid state and in solution, while 5 exists as a syn-conformer in similarity to the parent of 4,9-methanothia[11]annulene (3).

AB - First two derivatives of 4,9-methanothia[11]annulene, 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes (4 and 5), were synthesized from the diketosulfide 6. Spectroscopic properties and X-ray crystallographic analyses revealed that 4 exists as an anti-conformer in respect of stereochemical relationship between the methano bridge and the sulfur atom both in solid state and in solution, while 5 exists as a syn-conformer in similarity to the parent of 4,9-methanothia[11]annulene (3).

KW - Annulenes

KW - Conformation

KW - Density functional calculation

KW - Heterocycles

KW - X-ray crystal structures

UR - http://www.scopus.com/inward/record.url?scp=0037029825&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(02)00353-8

DO - 10.1016/S0040-4020(02)00353-8

M3 - 学術論文

AN - SCOPUS:0037029825

SN - 0040-4020

VL - 58

SP - 3647

EP - 3654

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Synthesis and conformation of 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes

Abstract

Keywords

ASJC Scopus subject areas

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