発表論文

2020

Takao Okazaki, Gaku Aoyama, Toshikazu Kitagawa
Brønsted Acid-Catalyzed Aldol Cyclotrimerization of 1-Indanones in Ionic Liquid: An Experimental and DFT Study of Substituent Effect
J. Phys. Org. Chem., 2021, 34(1), e4129/1-7.

Katsuyuki Hirai, Masao Yamaguchi, Takao Okazaki, Toshikazu Kitagawa, Hideo Tomioka
Phenyl(triazolyl)carbene Revisited. Unique Role of Triazolyl Group on Carbene Chemistry
J. Phys. Org. Chem., 2021, 34(6), e4187/1-15.

2019

Takao Okazaki, Takuya Matsunaga, Toshikazu Kitagawa
Charge delocalization mode and change in aromaticity of protonated 7-phenylbenzo[k]fluoranthenes studied by experimental observation and DFT calculations
J. Phys. Org. Chem., 2019, 32, e3998/1-8.

Shigeharu Wakabayashi, Natsu Sugiyama, Yasuhiro Ohki, Takahito Itoh, Toshikazu Kitagawa
3-[4’-(Diethylboryl)phenyl]pyridine: Exclusive Crystallization of the Cyclic Tetramer
Chem. Asian J., 2019, 14, 568-573.

2018

Toshikazu Kitagawa, Takashi Kawano, Takahiro Hase, Ikuma Hayakawa, Katsuyuki Hirai, Takao Okazaki
Electron-Transfer Properties of Phenyleneethynylene Linkers Bound to Gold via a Self-Assembled Monolayer of Molecular Tripod
Molecules, 2018, 23, 2893/1-2893/9.

Takao Okazaki, Ryota Nakanishi, Toshikazu Kitagawa
Effect of solvation of ionic liquid on Brønsted acid-catalyzed aldol cyclotrimerization of indanones and related cyclic ketones
J. Phys. Org. Chem., 2018, 31, e3887/1-e3887/8.

2017

Toshikazu Kitagawa, Shima Nakanishi, Aya Mizuno, Yohei Niwa, Hiroki Tabata, Katsuyuki Hirai, Takao Okazaki
Tuning the Coverage of Self-Assembled Monolayer by Introducing Bulky Substituents onto Rigid Adamantane Tripod
Archive Org. Chem., ARKIVOC, 2018, 131-144.

Takao Okazaki, Hiroyuki Yamamoto, Toshikazu Kitagawa
Ring-Closure Reaction of 2-Benzoylbenzenediazonium Salts in 1-Butyl-3-methylimidazolium Ionic Liquids
ARKIVOC, 2018, 50-59.

2016

Takao Okazaki, Yuki Yamamura, Takeshi Futemma, Toshikazu Kitagawa
Cationic Intermediates for Electrophilic Reactions from 9,9-Dimethyl-9H-9- silafluorene
Current Organic Chemistry, 2016, 21, 3014-3021.

Katsuyuki Hirai, Kana Bessho, Kosaku Tsujita, Toshikazu Kitagawa
Diphenylcarbene Protected by Four ortho-IodineGroups: An Unusually Persistent Triplet Carbene
Molecules , 2016, 21, 1545/1-1545/15.

Toshikazu Kitagawa, Takeshi Kawano
Self-Assembled Monolayer of Molecular Tripod as a Molecule-Electrode Junction
Proceedings of the 3rd International Conference on Chemical Innovation, 2016, pp. 74-77.

2015

Takao Okazaki, Koji Itoh, Toshikazu Kitagawa
Solvolysis of 2-Adamantyl p-Toluenesulfonate in Ionic Liquid 1-Butyl-3-methylimidazolium Tetrafluoroborate
Tetrahedron Lett., 2015, 56, 6066-6068.

Takao Okazaki, Madoka Nakagawa, Takeshi Futemma, Toshikazu Kitagawa
NMR and DFT Studies on Persistent Carbocations Derived from Benzo[kl]xanthene, Dibenzo[d,d']benzo[1,2-b:4,3-b']difuran, and Dibenzo[d,d']benzo[1,2-b:4,5-b']difuran in Superacidic Media
J. Phys. Org. Chem., 2015, 29, 107-111.

2014

Satoshi Katano, Yousoo Kim, Toshikazu Kitagawa, Maki Kawai
Single Molecule Study of the Electronic Structures of Molecular Tripods with Functional Units
J. Vac. Soc. Jpn., 2014, 57, 159-162.

Takao Okazaki, Madoka Nakagawa, Toshikazu Kitagawa, Kenneth K. Laali
Experimental NMR and DFT Studies of Persistent Carbocations Derived from Hetero-Polycyclic Aromatic Hydrocarbons Containing Oxygen Atom: Dibenzo[b,d]furan, Benzo[b]naphtho[1,2-d]furan, Benzo[b]naphtho[2,3-d]furan, Benzo[b]naphtho[2,1-d]furan, and Dinaphtho[2,1-b:1',2'-d]furan
Bull. Chem. Soc. Jpn., 2014, 87, 1235-1244.

Toshikazu Kitagawa, Hiroaki Matsubara, Takao Okazaki, Koichi Komatsu
Electrochemistry of the Self-Assembled Monolayers of Dyads Consisting of Tripod-Shaped Trithiol and Bithiophene on Gold
Molecules, 2014, 19, 15298-15313.

Takao Okazaki, Kenneth K. Laali, Scott D. Bunge, Sonya K. Adas
4-(Pentafluorosulfanyl)benzenediazonium Tetrafluoroborate: A Versatile Launch Pad for the Synthesis of Aromatic SF5 Compounds via Cross Coupling, Azo Coupling, Homocoupling, Dediazoniation, and Click Chemistry
Eur. J. Org. Chem., 2014, 1630-1644.

Takao Okazaki, Kenneth K. Laali, A. Srinivas Reddy
The 2,4-dimethyl-7-pentafluorosulfanyl-5-(trifluoromethyl)dibenzo[b,d]thiophenium trifluoromethanesulfonate: The SF5-analog of Umemoto salt
J. Fluorine Chem., 2014, 165, 91-95.

Takao Okazaki, Kenneth K. Laali
Mono- and dinitration of pentafluorosulfanylbenzenes with [NO2][BF4], and substrate selectivity (PhSF5 vs PhCF3 and PhSF5 vs PhNO2) in competitive nitration
J. Fluorine Chem., 2014, 165, 96-100.

2013

Satoshi Katano, Yousoo Kim, Toshikazu Kitagawa, Maki Kawai
Tailoring Electronic States of a Single Molecule Using Adamantane-based Molecular Tripods
Phys. Chem. Chem. Phys., 2013, 15, 14229-14233.

Takao Okazaki, Taisuke Adachi, Toshikazu Kitagawa
NMR and DFT Study on Onium Ions Derived from Substituted Fluoranthenes and Benzo[k]fluoranthenes
Bull. Chem. Soc. Jpn., 2013, 86, 464-471.

2012

Ideal Redox Behavior of the High-Density Self-Assembled Monolayer of a Molecular Tripod on a Au(111) Surface with a Terminal Ferrocene Group, Toshikazu Kitagawa, Hiroaki Matsubara, Koichi Komatsu, Katsuyuki Hirai, Takao Okazaki, Takahiro Hase, Langmuir, 2012, 29, 4275-4282.

2011

Kohei Ogawa, Koichi Komatsu, Toshikazu Kitagawa
Allyl Radical Nature of a Phenylcyclopentadienyl Radical Annelated with Two Homoadamantene Frameworks
J. Org. Chem., 2011, 76, 6095-6100.

Katsuyuki Hirai, Keiji Hatanaka, Tsuyoshi Yamaguchi, Akiko Miyajima, Toshikazu Kitagawa, Hideo Tomioka
Generation and Reactivities of Triplet Diphenylcarbenes Protected by Bulky Groups as para Substituents
J. Phys. Org. Chem., 2011, 24, 909-920.

2010

Hirai, K.; Bessho, K.; Kitagawa, T.; Tomioka, H.
Triplet Diphenylcarbene Protected by Iodine and Bromine Groups
J. Phys. Org. Chem., 2010, 23, 347-356.

Hanamura, M.; Kamada, J.; Amano, A.; Takeuchi, K.; Okazaki, T.; Hirai, K.; Kitagawa, T.
Self-Sensitized Photooxygenation of a C60-Cycloheptatriene Dyad to Form Norcaradiene-Derived Endoperoxides
Eur. J. Org. Chem., 2010, 3257-3264.

2009

北川敏一
アダマンタンで分子の三脚をつくる － 分子デバイスの“立役者”となるか？！
化学同人，64巻，3号，2009, pp. 49-53.

Laali,　K. K.; Okazaki,T.; Kitagawa,T.; Shinmyozu, T.
Stable-Ion NMR Spectroscopy and GIAO-DFT Study of Carbocations Derived from Multibridged [3_n]Cyclophanes
Eur. J. Org. Chem. 2009, 4451-4457.

Hirai,K.; Itoh,T.; Tomioka, H.
Persistent Triplet Carbenes
Chem. Rev. 2009, 109, 3275-3332.

2008

Wakabayashi, S.; Imamura, S.; Sugihara, Y.; Shimizu, M.; Kitagawa, T.; Ohki, Y.; Tatsumi, K.
3-(Dimethylboryl)pyridine: Synthesis, Structure, and Remarkable Steric Effects in Scrambling Reactions
J. Org. Chem. 2008, 73, 81-87.

Ogawa, K.; Minegishi, S.; Komatsu, K.; Kitagawa, T.
Generation and Reaction of a Phenyl-Substituted Cyclopentadienyl Cation Annelated with Two Homoadamantene, Frameworks
J. Org. Chem. 2008, 73, 5248-5254.

Katano, S.; Kim, Y.; Kitagawa, T.; Kawai, M.
Self Assembly and STM Tip-induced Motion of Ferrocene Adamantane Trithiolate Adsorbed on Au(111)
Jpn. J. Appl. Phys. 2008, 47, 6156-6159.

Murata, M.; Ochi, Y.; Kitagawa, T.; Komatsu, K.; Murata Y.
NMR Studies on Monofunctionalized Fullerenyl Cation and Anion Encapsulating a H₂ Molecule
Chem. Asian J. 2008, 3, 1336-1342.

Brule, C.; Sultana, F.; Hollenstein, S.; Okazaki, T.; Laali, K. K.
Superacid-Catalyzed Dimerization/Cyclization of Isopropenyl-PAHs - Novel Pathways to PAH Dimers, Phenalenes and Their Stable Carbocations
Eur. J. Org. Chem. 2008, 3700-3708.

Laali, K. K.; Okazaki, T.; Bunge, S. D.; Lenoir, D.
Stable Ion and Electrophilic Chemistry of the Sterically Crowded Stilbene 1,1'-Bi(benzocyclobutenylidene) and Its Derivatives
J. Org. Chem. 2008, 73, 4092-4100.

Laali, K. K.; Okazaki, T.; Sultana, F.; Bunge, S. D.; Banik, B. K.; Swartz, C.
Stable-Ion NMR and GIAO-DFT Study of the Carbocations from Benzofluorenes and Dibenzofluorenes; Synthesis of Nitro Derivatives; Mutagenicity Assay and X-ray Analysis
Eur. J. Org. Chem. 2008, 1740-1752.

Benassi, M.; Abdelnur, P. V.; Eberlin, M. N.; Okazaki, T.; Laali, K. K.
Intrinsic Gas-Phase Acidity and Electrophilicity of Model Heterocations and Carbocations Relative to Pyridine: Adduct Formation versus α- or β-(Proton Transfer) Elimination
Applied Catalysis, A, General 2008, 336, 116-127.

Laali, K. K.; Okazaki, T.; Mitchell, R. H.; Ayub, K.; Zhang, R.; Robinson, S. G.
Stable Ion NMR and GIAO-DFT Study of Novel Cations from 8,16-Dicyano[2.2]metacyclophanedienes and from Strategically Substituted/Benzannelated Dihydropyrenes: Charge-Induced Tropicity Modulation and p-Switching
J. Org. Chem. 2008, 73, 457-466.

Hubbard, A.; Okazaki, T.; Laali, K. K.
Halo- and Azidodediazoniation of Arenediazonium Tetrafluoroborates with Trimethylsilyl Halides and Trimethylsilyl Azide and Sandmeyer-Type Bromodediazoniation with Cu(I)Br in [BMIM][PF₆] Ionic Liquid
J. Org. Chem. 2008, 73, 316-319.

北川敏一（共著）
有機化学（奥山 格監修）
丸善，2008.

2007

Katano, S.; Kim, Y.; Matsubara, H.; Kitagawa, T.; Kawai, M.
Hierarchical Chiral Framework Based on a Rigid Adamantane Tripod on Au(111)
J. Am. Chem. Soc. 2007, 129, 2511-2515.

Kitagawa, T.
Generation, Stability, and Reactions of Alkylated Fullerene Cations
Recent Developments in Carbocation and Onium Ion Chemistry, Laali, K. K. ed., American Chemical Society, 2007, pp. 234-253.

Takahashi, Y.; Sakakibara, T.; Tominaga, T.; Inaba, M.; Tomioka, H.
New Facets in the Photochemistry and Thermal Reaction of 2,2-Diphenylmethylenecyclopropane
Journal of Photochem. Photobiol. A: Chem. 2007, 185, 253-262.

Kawano, M.; Hirai, K.; Tomioka, H.; Ohashi, Y.
Structure Determination of Triplet Diphenylcarbenes by in Situ X-ray Crystallographic Analysis
J. Am. Chem. Soc. 2007, 129, 2383-2391.

Itoh, T.; Hirai, K.; Tomioka H.
From Persistent Triplet Carbenes to Persistent High-Spin Polycarbenes
Bull. Chem. Soc. Jpn. 2007, 80, 138-157.

Hubbard, A.; Okazaki, T.; Laali, K. K.
Chlorination of Aromatics with Trichloroisocyanuric Acid (TCICA) in Bronsted-Acidic Imidazolium Ionic Liquid, [BMIM(SO3H)][OTf]: an Economical, Green Protocol for the Synthesis of Chloroarenes
Australian J. Chem. 2007, 60, 923-927.

Laali, K. K.; Chun, J.-H.; Okazaki, T.; Kumar, S.; Borosky, G. L.; Swartz, C.
Electrophilic Chemistry of Thia-PAHs: Stable Carbocations (NMR and DFT), S-Alkylated Onium Salts, Model Electrophilic Substitutions (Nitration and Bromination), and Mutagenicity Assay
J. Org. Chem. 2007, 72, 8383-8393.

Bae, S.; Mah, H.; Chaturvedi, S.; Jeknic, T. M.; Baird, W. M.; Katz, A. K.; Carrell, H. L.; Glusker, J. P.; Okazaki, T.; Laali, K. K.; Zajc, B.; Lakshman, M. K.
Synthetic, Crystallographic, Computational, and Biological Studies of 1,4-Difluorobenzo[c]phenanthrene and Its Metabolites
J. Org. Chem. 2007, 72, 7625-7633.

Laali, K. K.; Arrica, A.; Okazaki, T.; Harvey, R. G.
Substituent Effects in Benz[a]anthracene Carbocations: A Stable Ion, Electrophilic Substitution (Nitration, Bromination), and DFT Study
J. Org. Chem. 2007, 72, 6768-6775.

Laali, K. K.; Okazaki, T.; Bunge, S. D.
N-(Trifluoromethylsulfonyl)aryloxytrifluoromethylsulfoximines [ArO-SO(CF3)=NTf] and N-Aryltriflimides Ar-N(Tf)2 by Thermal and Photolytic Dediazoniation of [ArN2][BF4] in [BMIM][Tf2N] Ionic Liquid: Exploiting the Ambident Nucleophilic Character of a \"Nonnucleophilic\" Anion
J. Org. Chem. 2007, 72, 6758-6762.

Brule, C.; Laali, K. K.; Okazaki, T.; Lakshman, M. K.
Structure/Reactivity Relationships in the Benzo[c]phenanthrene Skeleton: Stable Ion and Electrophilic Substitution (Nitration, Bromination) Study of Substituted Analogues, Novel Carbocations and Substituted Derivatives
J. Org. Chem. 2007, 72, 3232-3241.

Brule, C.; Laali, K. K.; Okazaki, T.; Musafia, T.; Baird, W. M.
Stable Ion and Electrophilic Substitution (Nitration and Bromination) Study of A-ring Substituted Phenanthrenes: Novel Carbocations and Substituted Derivatives; NMR, X-ray Analysis, and Comparative DNA Binding
Eur. J. Org. Chem. 2007, 487-497.

Cabrini, L. G.; Benassi, M.; Eberlin, M. N.; Okazaki, T.; Laali, K. K.
R(Ar)O-N2+ vs. R(Ar)-N2O+: Are Alkoxy-(Aryloxy-)diazonium Ions or Alkyl-(Aryl-)N-nitroso-onium Ions Formed in the Gas-Phase Reactions of N2O with H+, Me+, Ph+, PhCH2+, Tr+ and PhCO+?
Eur. J. Org. Chem. 2007, 70-77.

北川敏一（共著）
大学院講義有機化学 演習編（野依良治ほか編）
東京化学同人，2007.

北川敏一
カルボカチオンにとどめを刺す － 超安定アニオンによる構造の解明
「化学」，化学同人，62巻，7号，2007, pp. 70-71.

平井克 幸
カルベンの化学―手が二本の炭素化学種は安定に存在できるのか？―，
「化学と教育」，日本化学会， 55巻，6号，2007， pp. 278-279.

2006

Kitagawa, T.; Idomoto, Y.; Matsubara, H.; Hobara, D.; Kakiuchi, T.; Okazaki, T.; Komatsu, K.
Rigid Molecular Tripod with an Adamantane Framework and Thiol Legs. Synthesis and Observation of an Ordered Monolayer on Au(111)
J. Org. Chem. 2006, 71, 1362-1369.

Takahashi, Y.; Sakakibara, T.; Inaba, M.; Tomioka, H.; Koseki, S.; Fujimoto, K.; Umeda, H.
Effect of Phenyl Substitution on the Lifetime and Product Distribution of Cyclobutylidene: Preference Change in the Rearrangements via 1,2-Carbon Shift and 1,2-Hydrogen Shift
Tetrahedron Lett. 2006, 47, 3995-3999.

Inada, T.; Funasaka, Y.; Kikuchi, K.; Takahashi, Y.; Ikeda, H.
Electron-Transfer Fluorescence Quenching of Aromatic Hydrocarbons by Europium and Ytterbium Ions in Acetonitrile
J. Phys. Chem. A 2006, 110, 2595-2600.

Itoh, T.; Nakata, Y.; Hirai, K.; Tomioka, H.
Triplet Diphenylcarbenes Protected by Trifluoromethyl and Bromine Groups. A Triplet Carbene Surviving a Day in Solution at Room Temperature
J. Am. Chem. Soc. 2006, 128, 957-967.

Hirai, K.; Kamiya, E.; Itoh, T.; Tomioka, H.
A Dendrimer Approach to High-Spin Polycarbenes. Conversion of Connectivity from Disjoint to Non-Disjoint by Perturbation of Nonbonding Molecular Orbital Coefficients
Org. Lett. 2006, 8, 1847-1850.

Okazaki, T.; Mandai, S.; Kitagawa, T.; Takeuchi, K.
Synthesis of Disubstituted Homodiamantanes by Acylative Ring Expansion Using Benzoyl Trifluoromethanesulfonate
Sci. Tech. Adv. Mater. 2006, 7, 531-535.

Kitagawa, T.; Murata, Y.; Komatsu K.
Fullerene Reactivity - Fullerene Cations and Open-Cage Fullerenes
Carbon-Rich Compounds. From Molecules to Materials, Haley, M. M.; Tykwinski, R. R. ed., Wiley-VCH, Weinheim, 2006, pp. 383-420.