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

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

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

1 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	859-863
Number of pages	5
Journal	Synthesis
Issue number	5
DOIs	https://doi.org/10.1055/s-1999-3461
State	Published - 1999

Keywords

Allenes
Cyclic acetylenes
Dynamic process
Eschenmoser-Tanabe fragmentation
Tosylhydrazone

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1055/s-1999-3461

Cite this

@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 -