Mitsunori Oda

Find an error

Name:

Organization: Shinshu University , Japan

Department: Department of Chemistry

Title: Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Cyclohepta[c]furan-based fluorophores: Synthesis, optical properties, solvatochromism and DFT study

Co-reporter:Tatsuya Yanagisawa, Naoki Kobayashi, Ryuta Miyatake, Mitsunori Oda

Dyes and Pigments 2017 Volume 143(Volume 143) pp:

Publication Date(Web):1 August 2017

DOI:10.1016/j.dyepig.2017.04.035

•6H-Cyclohepta[c]furan derivatives possessing aryl groups on 1,3-position as novel fluorophores were synthesized.•Their absorption and emission wavelengths were red-shifted by the substituents at 1,3-positions and 5,7-positions.•Theoretical calculations revealed that their photophysical behaviors are reproduced.Novel 6H-cyclohepta[c]furan derivatives possessing aryl groups on 1,3-position were synthesized, and their photophysical behavior were investigated. 1,3-Diphenyl-5,7-difomyl derivative showed solvatochromism. As the electron donating ability at 1,3-positions and the electron withdrawing ability at 5,7-positions increased, the absorption and emission wavelengths were bathochromically shifted. Theoretical calculations revealed that their photophysical behaviors are reproduced.

A Short-Step Synthesis of 1,6-Methano[10]annulene-3,4-dicarboximides and Their Benzene-, Naphthalene-, and Thiophene-Annulated Compounds (Eur. J. Org. Chem. 27/2014)

Co-reporter:Mitsunori Oda;Tomomi Nakamura;Miyako Neha;Daisuke Miyawaki;Akira Ohta;Shigeyasu Kuroda;Ryuta Miyatake

European Journal of Organic Chemistry 2014 Volume 2014( Issue 27) pp:

Publication Date(Web):

DOI:10.1002/ejoc.201490075

A Short-Step Synthesis of 1,6-Methano[10]annulene-3,4-dicarboximides and Their Benzene-, Naphthalene-, and Thiophene-Annulated Compounds

Co-reporter:Mitsunori Oda;Tomomi Nakamura;Miyako Neha;Daisuke Miyawaki;Akira Ohta;Shigeyasu Kuroda;Ryuta Miyatake

European Journal of Organic Chemistry 2014 Volume 2014( Issue 27) pp:5976-5985

Publication Date(Web):

DOI:10.1002/ejoc.201402776

Abstract

Triphenylphosphorane reagents 8 react with 1,3,5-cycloheptatriene-1,6-dicarbaldehyde (2) under acidic as well as basic conditions to produce 1,6-methano[10]annulene-3,4-dicarboximides 1 in moderate -to- good yields. The reagents 8 react with 3,4-arene-annulated 1,3,5-cycloheptatriene-1,6-dicarbaldehydes 9, 10, and 11 to afford only the Wittig condensation products under acidic conditions but produce the arene-annulated annulenedicarboximides under basic conditions. The structures of some of the dicarboximides and the intermediate Wittig condensation products were determined by X-ray structural analysis. The emission properties of the dicarboximides were also studied.

Synthesis, Molecular Structure, and Properties of 2-(2-Hydroxyphenyl)-1-azaazulene

Co-reporter:Mitsunori Oda;Ayumi Sugiyama;Rie Takeuchi;Yurie Fujiwara;Ryuta Miyatake;Takako Abe;Shigeyasu Kuroda

European Journal of Organic Chemistry 2012 Volume 2012( Issue 11) pp:2231-2236

Publication Date(Web):

DOI:10.1002/ejoc.201101831

Abstract

We herein report the synthesis of 2-(2-methoxyphenyl)-1-azaazulene (8) by a Suzuki–Miyaura cross-coupling reaction between 2-chloro-1-azaazulene and 2-methoxyphenylboronic acid and also by the condensation of tropone and the ylide derived from 1-(o-methoxyphenacyl)pyridinium iodide. Demethylation of 8 afforded the title compound 6. X-ray crystallographic analysis of 6 provided evidence for an intramolecular hydrogen bond between the phenolic hydrogen atom and the nitrogen atom of the azaazulenyl ring and also revealed its coplanar ring system. We also report the acidity, basicity, and absorption and emission behavior of 6.

Generation and spectroscopic properties of syn-1,6:9,14-bismethanodicyclodeca[cd,gh]pentalene dianion

Co-reporter:Shigeyasu Kuroda, Yoshihiro Terada, Ryuta Miyatake, Yoshikazu Horino, Takako Abe, Yurie Fujiwara, Mitsunori Oda

Tetrahedron Letters 2011 Volume 52(Issue 52) pp:7071-7074

Publication Date(Web):28 December 2011

DOI:10.1016/j.tetlet.2011.10.077

The hydrocarbon precursor, 8,16-dihydro-syn-1,6;9,14-bismethano[cd,gh]pentalene (5), to the title structure, dianion 4, was synthesized from ethyl 4-bromo-1,6-methano[10]annulene-3-carboxylate (6) in three steps, which included a nickel-catalyzed stereoselective homo-coupling, LiAlH4 reduction of the ester groups, and scandium triflate-catalyzed double intramolecular cyclization of the biarylmethyldiol. Deprotonation of 5 with n-butyllithium in THF-d8 provided 4, whose structure was confirmed by NMR analysis. Aspects of chemical shifts in the 1H NMR spectrum and the calculated structure of 4 establish its diatropic nature.

Synthesis, Stability, and Crystal Structure of an Azulenium Cation Containing an Adamantyl Group

Co-reporter:Mitsunori Oda;Nobue Nakajima;Nguyen Chung Thanh;Kazuhiro Kitahara;Ryuta Miyatake;Shigeyasu Kuroda

European Journal of Organic Chemistry 2008 Volume 2008( Issue 31) pp:5301-5307

Publication Date(Web):

DOI:10.1002/ejoc.200800700

Abstract

Starting from the trimethylsilyl enol ether of 1-acetyl-1,3,5-cycloheptatriene, the title 1H-azulenium cation was synthesized by a five-step sequence that involved a Noyori–Mukaiyama aldol reaction, a Nazarov cyclization, a Shapiro reaction, and a hydride abstraction. The Nazarov reaction of the aldol-type adduct resulted in the formation of an unusual double-bond position isomer, which has never been obtained in similar reactions forming tetrahydroazulenones. The pK_R⁺ value of the title cation was found to be 9.8, which is less than that expected by inductive stabilization from the number of carbons at the 1-position. The X-ray crystal structure of the title cation (ClO₄^– salt) reveals CH–O interactions and deformation of the azulenyl ion part.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)