Thermolytic fragmentation reactions of tricyclo[5.3.1.01,7]undeca- 2,4-dien-10-one Tosylhydrazone under basic conditions

Mitsunori Oda; Yoshimi Masaki; Shuichi Hayashi; Ryuta Miyatake; Shigeyasu Kuroda

doi:10.1055/s-1999-3461

Thermolytic fragmentation reactions of tricyclo[5.3.1.0^1,7]undeca- 2,4-dien-10-one Tosylhydrazone under basic conditions

Mitsunori Oda^*, Yoshimi Masaki, Shuichi Hayashi, Ryuta Miyatake, Shigeyasu Kuroda

^*この論文の責任著者

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研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

1 被引用数 (Scopus)

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Pyrolysis of tricyclo[5.3.1.0^1,7]undeca-2,4-dien-10-one tosylhydrazone (5) in the presence of base in an aprotic solvent gave the cyclic acetylene 6 and the allene 7, while that in the presence of sodium isopropoxide in isopropanol afforded the two isopropyl ethers, 8 and 9, along with 6 and none of 7. A dynamic process of methylene flipping in the acetylenic product 6 was also revealed.

本文言語	英語
ページ（範囲）	859-863
ページ数	5
ジャーナル	Synthesis
号	5
DOI	https://doi.org/10.1055/s-1999-3461
出版ステータス	出版済み - 1999

ASJC Scopus 主題領域

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有機化学

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10.1055/s-1999-3461

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@article{dc1616af992648a4bb0cd43b5f3f93cf,

title = "Thermolytic fragmentation reactions of tricyclo[5.3.1.01,7]undeca- 2,4-dien-10-one Tosylhydrazone under basic conditions",

abstract = "Pyrolysis of tricyclo[5.3.1.01,7]undeca-2,4-dien-10-one tosylhydrazone (5) in the presence of base in an aprotic solvent gave the cyclic acetylene 6 and the allene 7, while that in the presence of sodium isopropoxide in isopropanol afforded the two isopropyl ethers, 8 and 9, along with 6 and none of 7. A dynamic process of methylene flipping in the acetylenic product 6 was also revealed.",

keywords = "Allenes, Cyclic acetylenes, Dynamic process, Eschenmoser-Tanabe fragmentation, Tosylhydrazone",

author = "Mitsunori Oda and Yoshimi Masaki and Shuichi Hayashi and Ryuta Miyatake and Shigeyasu Kuroda",

year = "1999",

doi = "10.1055/s-1999-3461",

language = "英語",

pages = "859--863",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "5",

}

TY - JOUR

T1 - Thermolytic fragmentation reactions of tricyclo[5.3.1.01,7]undeca- 2,4-dien-10-one Tosylhydrazone under basic conditions

AU - Oda, Mitsunori

AU - Masaki, Yoshimi

AU - Hayashi, Shuichi

AU - Miyatake, Ryuta

AU - Kuroda, Shigeyasu

PY - 1999

Y1 - 1999

N2 - Pyrolysis of tricyclo[5.3.1.01,7]undeca-2,4-dien-10-one tosylhydrazone (5) in the presence of base in an aprotic solvent gave the cyclic acetylene 6 and the allene 7, while that in the presence of sodium isopropoxide in isopropanol afforded the two isopropyl ethers, 8 and 9, along with 6 and none of 7. A dynamic process of methylene flipping in the acetylenic product 6 was also revealed.

AB - Pyrolysis of tricyclo[5.3.1.01,7]undeca-2,4-dien-10-one tosylhydrazone (5) in the presence of base in an aprotic solvent gave the cyclic acetylene 6 and the allene 7, while that in the presence of sodium isopropoxide in isopropanol afforded the two isopropyl ethers, 8 and 9, along with 6 and none of 7. A dynamic process of methylene flipping in the acetylenic product 6 was also revealed.

KW - Allenes

KW - Cyclic acetylenes

KW - Dynamic process

KW - Eschenmoser-Tanabe fragmentation

KW - Tosylhydrazone

UR - http://www.scopus.com/inward/record.url?scp=0032914265&partnerID=8YFLogxK

U2 - 10.1055/s-1999-3461

DO - 10.1055/s-1999-3461

M3 - 学術論文

AN - SCOPUS:0032914265

SN - 0039-7881

SP - 859

EP - 863

JO - Synthesis

JF - Synthesis

IS - 5

ER -

Thermolytic fragmentation reactions of tricyclo[5.3.1.01,7]undeca- 2,4-dien-10-one Tosylhydrazone under basic conditions

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引用スタイル

Thermolytic fragmentation reactions of tricyclo[5.3.1.0^1,7]undeca- 2,4-dien-10-one Tosylhydrazone under basic conditions