Duplicated ring enlargement of 4,9-methanothia[11]annulene to 6,11-methanothia[15]annulene

Shigeyasu Kuroda; Rie Kasai; Ryo Nagaya; Ryuta Miyatake; Yoshikazu Horino; Naoko Matsumoto; Mitsunori Oda

doi:10.1016/j.tetlet.2010.11.072

Duplicated ring enlargement of 4,9-methanothia[11]annulene to 6,11-methanothia[15]annulene

Shigeyasu Kuroda^*, Rie Kasai, Ryo Nagaya, Ryuta Miyatake, Yoshikazu Horino, Naoko Matsumoto, Mitsunori Oda

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

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

Abstract

3,10-Dipyrrolidinyl-4,9-methanothia[11]annulene reacts with excess dimethyl acetylenedicarboxylate (DMAD) in refluxing toluene to give ring-enlarged 6,11-methanothia[15]annulene. X-ray crystallographic analysis of the product shows two different cis,trans-dienyl parts in the ring system. Product formation possibly involves π-facial selective addition of the enamine with DMAD and torque-selective ring opening of the intermediate cyclobutenes.

Original language	English
Pages (from-to)	1426-1429
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	13
DOIs	https://doi.org/10.1016/j.tetlet.2010.11.072
State	Published - 2011/03/30

Keywords

Cycloaddition
Electrocyclic reaction
Enamine
Methanothia-annulene
X-ray crystallographic analysis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.11.072

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@article{b21608b7f8ab4d25bcc1075a5d7e7172,

title = "Duplicated ring enlargement of 4,9-methanothia[11]annulene to 6,11-methanothia[15]annulene",

abstract = "3,10-Dipyrrolidinyl-4,9-methanothia[11]annulene reacts with excess dimethyl acetylenedicarboxylate (DMAD) in refluxing toluene to give ring-enlarged 6,11-methanothia[15]annulene. X-ray crystallographic analysis of the product shows two different cis,trans-dienyl parts in the ring system. Product formation possibly involves π-facial selective addition of the enamine with DMAD and torque-selective ring opening of the intermediate cyclobutenes.",

keywords = "Cycloaddition, Electrocyclic reaction, Enamine, Methanothia-annulene, X-ray crystallographic analysis",

author = "Shigeyasu Kuroda and Rie Kasai and Ryo Nagaya and Ryuta Miyatake and Yoshikazu Horino and Naoko Matsumoto and Mitsunori Oda",

note = "Funding Information: This research was carried out in part under financial support from Kyowa Hakko Chemical Co. Inc. (for S.K.). A financial support from the Faculty of Science at Shinshu University (for M.O.) is also acknowledged. ",

year = "2011",

month = mar,

day = "30",

doi = "10.1016/j.tetlet.2010.11.072",

language = "英語",

volume = "52",

pages = "1426--1429",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "13",

}

TY - JOUR

T1 - Duplicated ring enlargement of 4,9-methanothia[11]annulene to 6,11-methanothia[15]annulene

AU - Kuroda, Shigeyasu

AU - Kasai, Rie

AU - Nagaya, Ryo

AU - Miyatake, Ryuta

AU - Horino, Yoshikazu

AU - Matsumoto, Naoko

AU - Oda, Mitsunori

N1 - Funding Information: This research was carried out in part under financial support from Kyowa Hakko Chemical Co. Inc. (for S.K.). A financial support from the Faculty of Science at Shinshu University (for M.O.) is also acknowledged.

PY - 2011/3/30

Y1 - 2011/3/30

N2 - 3,10-Dipyrrolidinyl-4,9-methanothia[11]annulene reacts with excess dimethyl acetylenedicarboxylate (DMAD) in refluxing toluene to give ring-enlarged 6,11-methanothia[15]annulene. X-ray crystallographic analysis of the product shows two different cis,trans-dienyl parts in the ring system. Product formation possibly involves π-facial selective addition of the enamine with DMAD and torque-selective ring opening of the intermediate cyclobutenes.

AB - 3,10-Dipyrrolidinyl-4,9-methanothia[11]annulene reacts with excess dimethyl acetylenedicarboxylate (DMAD) in refluxing toluene to give ring-enlarged 6,11-methanothia[15]annulene. X-ray crystallographic analysis of the product shows two different cis,trans-dienyl parts in the ring system. Product formation possibly involves π-facial selective addition of the enamine with DMAD and torque-selective ring opening of the intermediate cyclobutenes.

KW - Cycloaddition

KW - Electrocyclic reaction

KW - Enamine

KW - Methanothia-annulene

KW - X-ray crystallographic analysis

UR - http://www.scopus.com/inward/record.url?scp=79951950579&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.11.072

DO - 10.1016/j.tetlet.2010.11.072

M3 - 学術論文

AN - SCOPUS:79951950579

SN - 0040-4039

VL - 52

SP - 1426

EP - 1429

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

Duplicated ring enlargement of 4,9-methanothia[11]annulene to 6,11-methanothia[15]annulene

Abstract

Keywords

ASJC Scopus subject areas

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