Synthesis, properties and molecular structure of a novel dicyanoheptafulvene derivative, 4′-dicyanomethylidenedispiro[cyclohexane- 1, 1′-(1′,4′,7′-trihydrocyclopenta[f]azulene)-7′, 1″-cyclohexane]

Nguyen Chung Thanh; Ryuta Miyatake; Hitoshi Kainuma; Shigeyasu Kuroda; Mitsunori Oda

doi:10.1016/j.tet.2005.10.015

Synthesis, properties and molecular structure of a novel dicyanoheptafulvene derivative, 4′-dicyanomethylidenedispiro[cyclohexane- 1, 1′-(1′,4′,7′-trihydrocyclopenta[f]azulene)-7′, 1″-cyclohexane]

Nguyen Chung Thanh, Ryuta Miyatake, Hitoshi Kainuma, Shigeyasu Kuroda, Mitsunori Oda^*

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

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

2 Scopus citations

Abstract

A novel dicyanoheptafulvene 9 annulated by two spiro[4,5]deca-1,3-dienes was synthesized by the reaction of dispirocyclopentaazulenium cation 8 with bromomalononitrile. Although 9 was found to have a nonplanar heptafulvene structure by its X-ray crystallographic analysis, it is still capable of π-conjugation and thus shows appreciable contribution of the dipolar resonance form 9B based on its spectroscopic data. The degree of the contribution was further evaluated for various dicyanoheptafulvenes in terms of the partial sum of atomic charges of the dicyanomethylene group in the calculated structures besides the interplanar angles of the heptafulvene part and the length of the exocyclic double bond in the crystal structures.

Original language	English
Pages (from-to)	586-593
Number of pages	8
Journal	Tetrahedron
Volume	62
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2005.10.015
State	Published - 2006/01/23

Keywords

Carbenium ions
Cyclopenta[f]azulenes
Density functional calculation
Heptafulvene
X-ray crystal structures

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{a897b90d4e6247fea4897a8883ffe604,

title = "Synthesis, properties and molecular structure of a novel dicyanoheptafulvene derivative, 4′-dicyanomethylidenedispiro[cyclohexane- 1, 1′-(1′,4′,7′-trihydrocyclopenta[f]azulene)-7′, 1″-cyclohexane]",

abstract = "A novel dicyanoheptafulvene 9 annulated by two spiro[4,5]deca-1,3-dienes was synthesized by the reaction of dispirocyclopentaazulenium cation 8 with bromomalononitrile. Although 9 was found to have a nonplanar heptafulvene structure by its X-ray crystallographic analysis, it is still capable of π-conjugation and thus shows appreciable contribution of the dipolar resonance form 9B based on its spectroscopic data. The degree of the contribution was further evaluated for various dicyanoheptafulvenes in terms of the partial sum of atomic charges of the dicyanomethylene group in the calculated structures besides the interplanar angles of the heptafulvene part and the length of the exocyclic double bond in the crystal structures.",

keywords = "Carbenium ions, Cyclopenta[f]azulenes, Density functional calculation, Heptafulvene, X-ray crystal structures",

author = "Thanh, {Nguyen Chung} and Ryuta Miyatake and Hitoshi Kainuma and Shigeyasu Kuroda and Mitsunori Oda",

note = "Funding Information: We thank Mr. Takuya Uchiyama at Toyama University for preliminary calculations of heptafulvene derivatives. The present work was supported by a Grant-in-Aid for Scientific Research (No. 13640528) from the Ministry of Education, Sports, Culture, Science and Technology, Japan. ",

year = "2006",

month = jan,

day = "23",

doi = "10.1016/j.tet.2005.10.015",

language = "英語",

volume = "62",

pages = "586--593",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "4",

}

Synthesis, properties and molecular structure of a novel dicyanoheptafulvene derivative, 4′-dicyanomethylidenedispiro[cyclohexane- 1, 1′-(1′,4′,7′-trihydrocyclopenta[f]azulene)-7′, 1″-cyclohexane]. / Thanh, Nguyen Chung; Miyatake, Ryuta; Kainuma, Hitoshi et al.
In: Tetrahedron, Vol. 62, No. 4, 23.01.2006, p. 586-593.

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

TY - JOUR

T1 - Synthesis, properties and molecular structure of a novel dicyanoheptafulvene derivative, 4′-dicyanomethylidenedispiro[cyclohexane- 1, 1′-(1′,4′,7′-trihydrocyclopenta[f]azulene)-7′, 1″-cyclohexane]

AU - Thanh, Nguyen Chung

AU - Miyatake, Ryuta

AU - Kainuma, Hitoshi

AU - Kuroda, Shigeyasu

AU - Oda, Mitsunori

N1 - Funding Information: We thank Mr. Takuya Uchiyama at Toyama University for preliminary calculations of heptafulvene derivatives. The present work was supported by a Grant-in-Aid for Scientific Research (No. 13640528) from the Ministry of Education, Sports, Culture, Science and Technology, Japan.

PY - 2006/1/23

Y1 - 2006/1/23

N2 - A novel dicyanoheptafulvene 9 annulated by two spiro[4,5]deca-1,3-dienes was synthesized by the reaction of dispirocyclopentaazulenium cation 8 with bromomalononitrile. Although 9 was found to have a nonplanar heptafulvene structure by its X-ray crystallographic analysis, it is still capable of π-conjugation and thus shows appreciable contribution of the dipolar resonance form 9B based on its spectroscopic data. The degree of the contribution was further evaluated for various dicyanoheptafulvenes in terms of the partial sum of atomic charges of the dicyanomethylene group in the calculated structures besides the interplanar angles of the heptafulvene part and the length of the exocyclic double bond in the crystal structures.

AB - A novel dicyanoheptafulvene 9 annulated by two spiro[4,5]deca-1,3-dienes was synthesized by the reaction of dispirocyclopentaazulenium cation 8 with bromomalononitrile. Although 9 was found to have a nonplanar heptafulvene structure by its X-ray crystallographic analysis, it is still capable of π-conjugation and thus shows appreciable contribution of the dipolar resonance form 9B based on its spectroscopic data. The degree of the contribution was further evaluated for various dicyanoheptafulvenes in terms of the partial sum of atomic charges of the dicyanomethylene group in the calculated structures besides the interplanar angles of the heptafulvene part and the length of the exocyclic double bond in the crystal structures.

KW - Carbenium ions

KW - Cyclopenta[f]azulenes

KW - Density functional calculation

KW - Heptafulvene

KW - X-ray crystal structures

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U2 - 10.1016/j.tet.2005.10.015

DO - 10.1016/j.tet.2005.10.015

M3 - 学術論文

AN - SCOPUS:28844501393

SN - 0040-4020

VL - 62

SP - 586

EP - 593

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -