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高度官能基化オキセタンの選択的合成反応
(Selective Synthesis of Highly Functionalized
Oxetanes)
安倍 学
使える！有機合成反応 実践の手引き，No. 101
（株）化学同人，印刷中
Generation and Intermolecular Trapping of
1,2-Diaza-4-silacyclopentane-3,5-diyls in the Denitrogenation of
2,3,5,6-Tetraaza-7-silabicyclo[2.2.1]hept-2-ene: An Experimental and
Computational Study.
Takeshi Nakamura, Akinobu Takegami, and Manabu
Abe*
submitted
Stereoselective Triplet
Sensitized Radical Reactions of Furanone Derivatives.
Rabih Jahjah, Abdoulaye
Gassama, Veronique Bulach, Chikako Suzuki, Manabu Abe,* Norbert Hoffmann,*
Agathe Martinez, Jean-Marc Nuzillard
Chem. Eur. J., in press
Computational Study of the
Cooperative Effects of Nitrogen and Silicon Atoms on the Singlet-Triplet Energy
Spacing in 1,3-Diradicals and the Reactivity of their Singlet States.
Nakamura, Takeshi, Gagliardi, Laura, Abe, Manabu*
J. Phys. Org. Chem. in
press.
Formation of a 4-membered ring III (Oxetanes)
Abe,
Manabu.
in Handbook of Synthetic Photochemistry, Albini Ed., Wiley-VCH,
2009.
一重項ジラジカル化学への期待-ファジーな結合が拓く有機化学の新たな道-
安倍 学
化学, 2009, 64 (6),
12-16
Yabuno, Youhei; Abe, Manabu; Hiraga, Yoshikazu
Site- and Stereoselectivity in the Photochemical Oxetane Formation Reaction
(Paterno-Buchi Reaction) of Tetrahydrobenzofuranols with Benzophenone:
Hydroxy-directed Diastereoselectivity?
Chemistry Letters (2008), 37 (8), 822-823..
Nakamura, Tsutomu; Yamamoto, Takahiko; Abe, Manabu; Matsumura, Hiroshi;
Hagihara, Yoshihisa; Goto, Tadashi; Yamaguchi, Takafumi; Inoue, Tsuyoshi
Oxidation of Srchael Peroxiredoxin Involves a Hypervalent Sulfur Intermediate
Proceedings of the National Academy of Science of the United States of
America (2008), 105 (17), 6238-6242.
Abe, Manabu
Recent Progress Regarding Regio, Site, and Stereoselective Formation of
Oxetanes in Paterno-Buchi Reactions.
Journal of Chinese Chemical Society (2008), 55 (3), 479-486. (Invited Paper)
Hamaguchi, Masashi, Nakaishi, Masahiro; Nagai, Toshikazu; Nakamura, Takeshi;
Abe, Manabu
Notable Effect of an Electron-Withdrawing Group at C3 on the Selective
Formation
of Alkylidenecyclobutanes in the Thermal Denitrogenation of 4-Spirocyclopropane-1-Pyrazolines.
Nonstatistical Dynamics Effects in the Denitrogenation Reactions
Journal of the American Chemical Society (2007), 129 (43), 12981-12988..
Moiseev, Andrey G.; Abe, Manabu; Danilov, Evgeny O.; Neckers, Douglas C.
First Direct Detection of 2,3-Dimethyl-2,3-diphenylcyclopropanone.
Journal of Organic Chemistry (2007), 72(8), 2777-2784.
Abe, Manabu.
New development of reactive intermediate chemistry: a case study of singlet
biradicals.
Yuki Gosei Kagaku Kyokaishi (2007), 65(1), 16-22.
Abe, Manabu; Kubo, Emi; Nozaki, Koichi; Matsuo, Takashi; Hayashi, Takashi.
An extremely long-lived singlet 4,4-dimethoxy-3,5-diphenylpyrazolidine-3,5-diyl
derivative: a notable nitrogen-atom effect on intra- and intermolecular
reactivity.
Angewandte Chemie, International Edition (2006), 45(46), 7828-7831.
Abe, Manabu; Taniguchi, Kana; Hayashi, Takashi.
Exo-Selective formation of bicyclic oxetanes in the photocycloaddition
reaction of carbonyl compounds with vinylene carbonate: the important role
of intermediary triplet diradicals in the stereoselectivity.
ARKIVOC (Gainesville, FL, United States) (2007), (8), 58-65.
Abe, Manabu; Kawanami, Satoshi; Masuyama, Araki; Hayashi, Takashi.
A Matrix Isolation Study of 2-Isopropylidenecyclopentane-1,3-diyl (Berson-Type
Diradical).
Journal of Organic Chemistry (2006), 71(17), 6607-6610.
Abe, Manabu; Hattori, Masanori; Takegami, Akinobu; Masuyama, Araki; Hayashi,
Takashi; Seki, Shu; Tagawa, Seiichi.
Experimental Probe for Hyperconjugative Resonance Contribution in Stabilizing
the Singlet State of 2,2-Dialkoxy-1,3-diyls: Regioselective 1,2-Oxygen
Migration.
Journal of the American Chemical Society (2006), 128(24), 8008-8014.
Abe, Manabu.
Less reactive triplet carbenes.
Kagaku (Kyoto, Japan) (2006), 61(5), 62-63.
Abe, Manabu; Terazawa, Midori; Nozaki, Koichi; Masuyama, Araki; Hayashi,
Takashi.
Notable temperature effect on the stereoselectivity in the photochemical
[2+2] cycloaddition reaction (Paterno-Buechi reaction) of 2,3-dihydrofuran-3-ol
derivatives with benzophenone.
Tetrahedron Letters (2006), 47(15), 2527-2530.
Masuyama, Araki; Yamaguchi, Takashi; Abe, Manabu; Nojima, Masatomo.
Alternative protocol for oxidation in water: an effective epoxidation system
promoted by the combination of Oxone and an amphiphilic ketone.
Tetrahedron Letters (2005), 46(2), 213-216.
Abe, Manabu; Ishihara, Chizuko; Kawanami, Satoshi; Masuyama, Araki.
Novel Substituent Effects on the Mechanism of the Thermal Denitrogenation
of 2,3-Diazabicyclo[2.2.1]hept-2-ene Derivatives, Stepwise versus Concerted.
Journal of the American Chemical Society (2005), 127(1), 10-11.
Griesbeck, Axel G.; Abe, Manabu; Bondock, Samir.
Selectivity Control in Electron Spin Inversion Processes: Regio- and Stereochemistry
of Paterno-Buechi Photocycloadditions as a Powerful Tool for Mapping Intersystem
Crossing Processes.
Accounts of Chemical Research (2004), 37(12), 919-928.
Abe, Manabu; Ishihara, Chizuko; Tagegami, Akinobu.
Theoretical Calculations of the Effects of 2-Heavier Group 14 Element and
Substituents on the Singlet-Triplet Energy Gap in Cyclopentane-1,3-diyls
and Computational Prediction of the Reactivity of Singlet 2-Silacyclopentane-1,3-diyls.
Journal of Organic Chemistry (2004), 69(21), 7250-7255.
Abe, Manabu; Kawanami, Satoshi; Ishihara, Chizuko; Nojima, Masatomo.
2-Silyl Group Effect on the Reactivity of Cyclopentane-1,3-diyls. Intramolecular
Ring-Closure versus Silyl Migration.
Journal of Organic Chemistry (2004), 69(17), 5622-5626.
Abe, Manabu; Torii, Etsuko; Nojima., Masatomo.
Patern-o-Buechi Photocyclization of 2-Siloxyfurans and Carbonyl Compounds.
Notable Substituent and Carbonyl (Aldehyde vs Ketone and Singlet- vs Triplet-Excited
State) Effects on the Regioselectivity (Double-Bond Selection) in the Formation
of Bicyclic exo-Oxetanes.
Journal of Organic Chemistry (2004), 69(6), 2228.
Abe, Manabu; Kawakami, Takanori; Ohata, Shinji; Nozaki, Koichi; Nojima,
Masatomo.
Mechanism of Stereo- and Regioselectivity in the Paterno-Buechi Reaction
of Furan Derivatives with Aromatic Carbonyl Compounds: Importance of the
Conformational Distribution in the Intermediary Triplet 1,4-Diradicals.
Journal of the American Chemical Society (2004), 126(9), 838-2846.
Abe, Manabu; Adam, Waldemar; Borden, Weston Thatcher; Hattori, Masanori;
Hrovat, David A.; Nojima, Masatomo; Nozaki, Koichi; Wirz, Jakob.
Effects of Spiroconjugation on the Calculated Singlet-Triplet Energy Gap
in 2,2-Dialkoxycyclopentane-1,3-diyls and on the Experimental Electronic
Absorption Spectra of Singlet 1,3-Diphenyl Derivatives. Assignment of the
Lowest-Energy Electronic Transition of Singlet Cyclopentane-1,3-diyls.
Journal of the American Chemical Society (2004), 126(2), 574-582.
Abe, Manabu. Photochemical oxetane formation: addition to heterocycles.
CRC Handbook of Organic Photochemistry and Photobiology (2nd Edition) (2004),
62/1-62/10.
Zhang, Daisy Y.; Hrovat, David A.; Abe, Manabu; Borden, Weston Thatcher.
DFT Calculations on the Effects of Para Substituents on the Energy Differences
between Singlet and Triplet States of 2,2-Difluoro-1,3-diphenylcyclopentane-1,3-diyls.
Journal of the American Chemical Society (2003), 125(42), 12823-12828.
Tokuyasu, Takahiro; Kunikawa, Shigeki; Abe, Manabu; Masuyama, Araki; Nojima,
Masatomo; Kim, Hye-Sook; Begum, Khurshida; Wataya, Yusuke.
Synthesis of Antimalarial Yingzhaosu A Analogues by the Peroxidation of
Dienes with Co(II)/O2/Et3SiH.
Journal of Organic Chemistry (2003), 68(19), 7361-7367.
Abe, Manabu; Ishihara, Chizuko; Nojima, Masatomo.
DFT Prediction of Ground-State Spin Multiplicity of Cyclobutane-1,3-diyls:
Notable Effects of Two Sets of Through-Bond Interactions.
Journal of Organic Chemistry (2003), 68(4), 1618-1621.
Abe, Manabu; Adam, Waldemar; Minamoto, Takafumi; Ino, Yasunori; Nojima,
Masatomo.
Mechanism of an Alcohol-Trapping Reaction in the Direct and Benzophenone-Sensitized
Photodenitrogenation of a Spiroepoxy-Substituted Azoalkane: Solvent Effects
and Stereochemical Deuterium Labeling.
Journal of Organic Chemistry (2003), 68(5), 1796-1803.
Abe, Manabu; Minamoto, Takafui; Ino, Yasunori; Kawakami, Takanori; Nojima,
Masatomo.
Reaction of 7,7-diphenyl-6-oxabicyclo[3.2.0]hept-1-ene with ROH; controlling
factors on the regioselectivity in the nucleophilic addition reaction.
Tetrahedron (2002), 58(35), 7043-7047.
Arakawa, Kazuhito; Endo, Yoshio; Kimura, Masashi; Yoshida, Takanori; Kitaoka,
Takeshi; Inakazu, Tomoyasu; Nonami, Yuji; Abe, Manabu; Masuyama, Araki;
Nojima, Masatomo; Sasaki, Takuma.
Multifunctional anti-angiogenic activity of the cyclic peroxide ANO-2 with
antitumor activity.
International Journal of Cancer (2002), 100(2), 220-227.
Abe, Manabu; Adam, Waldemar; Hara, Michihiro; Hattori, Masanori; Majima,
Tetsuro; Nojima, Masatomo; Tachibana, Kei; Tojo, Sachiko.
On the Electronic Character of Localized Singlet 2,2-Dimethoxycyclopentane-1,3-diyl
Diradicals: Substituent Effects on the Lifetime.
Journal of the American Chemical Society (2002), 124(23), 6540-6541.
Kawamura, Shin-ichi; Yamakoshi, Hideyuki; Abe, Manabu; Masuyama, Araki;
Nojima, Masatomo.
Ozonolyses of 1-alkyl-substituted 1-tert-butylethylenes and highly methylated
methylenecycloalkanes. The influence of the substituent steric bulk on
the direction of cleavage of the primary ozonides.
Tetrahedron (2002), 58(5), 891-896.
Abe, Manabu; Nojima, Masatomo.
Paterno-Buchi [2+2] photocycloaddition reactions of silyl ketene acetals:
Controlling factors on the regio- and stereoselectivity in the oxetane
formations.
Yuki Gosei Kagaku Kyokaishi (2001), 59(9), 855-865.
Abe, Manabu; Nojima, Masatomo.
Memory of chirality in photochemical reactions.
Kokagaku (2000), 31(1), 28-29.
Abe, Manabu; Tachibana, Kei; Fujimoto, Kiyotada; Nojima, Masatomo.
Regioselective formation of 3-selanyl-3-siloxyoxetanes in the Paterno-Buchi
reaction of silyl O,Se-ketene acetals (O,Se-SKA).
Synthesis (2001), (8), 1243-1247.
Mori, Atsushi; Abe, Manabu; Nojima, Masatomo.
Regioselective Oxygenations of S-Trans Dienes, Silyl Dienol Ethers (SDEs),
by Triphenyl Phosphite Ozonide (TPPO) and Its Mechanistic Study.
Journal of Organic Chemistry (2001), 66(10), 3548-3553.
Abe, Manabu.
New development of localized 1,3-biradicals. Oxygen atom effects on most
stable spin multiplicity and reactivity.
Kagaku to Kogyo (Tokyo) (2001), 54(2), 164-167.
Abe, Manabu; Torii, Etsuko; Nojima, Masatomo.
Lewis acid promoted ring-opening reactions of 2-methoxy-2-siloxyoxetane
in the presence of allylsilane: notable lewis acid effect on the ring-opening
regioselectivity of the oxetane.
Main Group Metal Chemistry (2000), 23(11), 651-654.
Abe, Manabu; Adam, Waldemar; Ino, Yasunori; Nojima, Masatomo.
Stereochemical Deuterium Labeling as Mechanistic Probe for Differentiating
the Singlet- and Triplet-Diradical Spin States in the Rearrangement of
the 2-Spiroepoxy-1,3-cyclopentanediyl to Oxetanes.
Journal of the American Chemical Society (2000), 122(27), 6508-6509.
Abe, Manabu; Torii, Etsuko; Nojima, Masatomo.
Paterno-Buechi Photocyclization of 2-Siloxyfurans and Carbonyl Compounds.
Notable Substituent and Carbonyl (Aldehyde vs Ketone and Singlet- vs Triplet-Excited
State) Effects on the Regioselectivity (Double-Bond Selection) in the Formation
of Bicyclic exo-Oxetanes.
Journal of Organic Chemistry (2000), 65(11), 3426-3431.
Abe, Manabu; Fujimoto, Kiyotada; Nojima, Masatomo.
Notable Sulfur Atom Effects on the Regio- and Stereoselective Formation
of Oxetanes in Paterno-Buechi Photocycloaddition of Aromatic Aldehydes
with Silyl O,S-Ketene Acetals.
Journal of the American Chemical Society (2000), 122(17), 4005-4010.
Abe, Manabu; Adam, Waldemar; Heidenfelder, Thomas; Nau, Werner M.; Zhang,
Xiangyang.
Intramolecular and Intermolecular Reactivity of Localized Singlet Diradicals:
The Exceedingly Long-Lived 2,2-Diethoxy-1,3-diphenylcyclopentane-1,3-diyl.
Journal of the American Chemical Society (2000), 122(9), 2019-2026.
Einaga, Hiroyuki; Nojima, Masatomo; Abe, Manabu.
Photooxygenation (Electron transfer) of silyl enol ethers derived from
1-indanone: silyl group and medium effects on the competitive formation
of 3-siloxy-1,2-dioxetane and -peroxy ketone.
Main Group Metal Chemistry (1999), 22(9), 539-543.
Einaga, Hiroyuki; Nojima, Masatomo; Abe, Manabu.
Photooxygenation (1O2) of silyl enol ethers derived from indan-1-ones:
competitive formation of tricyclic 3-siloxy-1,2-dioxetane and -silylperoxy
ketone.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic
Chemistry (1999), (17), 2507-2512.
Abe, Manabu; Inakazu, Tomoyasu; Munakata, Johichi; Nojima, Masatomo.
18O-Tracer Studies of Fe(II)-Induced Decomposition of 1,2,4-Trioxolanes
(Ozonides) Derived from Cyclopentenes and Indenes. Inner-Sphere Electron
Transfer Reduction of the Peroxide Linkage.
Journal of the American Chemical Society (1999), 121(28), 6556-6562.
Oku, Akira; Miki, Toshiyuki; Abe, Manabu; Ohira, Masatoshi; Kamada, Tohru.
Donor-Acceptor Binary Photocatalysis System Illustrated by the Intramolecular
Cyclization of a Cyclopropanone Acetal Tethered to Cyclohexen-2-one.
Bulletin of the Chemical Society of Japan (1999), 72(3), 511-517.
Abe, Manabu; Adam, Waldemar; Nau, Werner M.
Photochemical Generation and Methanol Trapping of Localized 1,3 and 1,4
Singlet Diradicals Derived from a Spiroepoxy-Substituted Cyclopentane-1,3-diyl.
Journal of the American Chemical Society (1998), 120(44), 11304-11310.
Abe, Manabu; Ikeda, Masayuki; Nojima, Masatomo.
A stereoselective, tandem [2+2] photocycloaddition-hydrolysis route to
aldol-type adducts.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic
Chemistry (1998), (19), 3261-3266.
Abe, Manabu; Shirodai, Yasuo; Nojima, Masatomo.
Regioselective formation of 2-alkoxyoxetanes in the photoreaction of aromatic
carbonyl compounds with -dimethyl ketene silyl acetals: notable solvent
and silyl group effects.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic
Chemistry (1998), (19), 3253-3260.
Abe, Manabu; Adam, Waldemar.
Electronic substituent effects on the EPR-spectral D parameter of trimethylenemethane
(TMM) triplet diradicals compared with localized cyclopentane-1,3-diyls.
Journal of the Chemical Society, Perkin Transactions 2: Physical Organic
Chemistry (1998), (5), 1063-1068.
Abe, Manabu; Sumida, Yohko; Nojima, Masatomo.
Notable Substituent Electronic Effects on the Regioselectivity of an Oxygen-Atom
Abstraction in the Reaction of Unsymmetrically Substituted Monocyclic 1,2-Dioxolanes
with Triphenylphosphine.
Journal of Organic Chemistry (1997), 62(3), 752-754.
Abe, Manabu; Ikeda, Masayuki; Shirodai, Yasuo; Nojima, Masatomo.
Regioselective and stereoselective formation of 2-siloxy-2-alkoxyetanes
in the photoreaction of cyclic ketene silyl acetals with 2-naphthaldehyde
and their transformation to aldol-type adducts.
Tetrahedron Letters (1996), 37(33), 5901-5904.
Abe, Manabu; Nojima, Masatomo; Oku, Akira.
Photoinduced electron transfer reactions of cyclopropanone acetal with
conjugated enones in the presence of a redox-type photosensitizer.
Tetrahedron Letters (1996), 37(11), 1833-6.
Kamada, Tohru; Ge-Qing; Abe, Manabu; Oku, Akira.
Selectivity in the ring-expansion and ring-switching reactions of bicyclooxonium
ions.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic
Chemistry (1996), (5), 413-16.
Abe, Manabu; Oku, Akira.
Oxidative Ring-Opening Reaction of Cyclopropanone Acetals with Carbonyl
Compounds via Photoinduced Electron Transfer. Generation of a -Carbonyl
Radical Species and Its Application to the Synthesis of -Hydroxy Ester
Derivatives.
Journal of Organic Chemistry (1995), 60(10), 3065-73.
Abe, Manabu; Oku, Akira.
Photoinduced electron transfer reaction of cyclpropanone acetals with arylmethyl
methanesulfonate: generation of beta-keto radical species and application
to C-C bond formation.
Journal of the Chemical Society, Chemical Communications (1994), (23),
2738.
Oku, Akira; Abe, Manabu; Iwamoto, Masaharu.
Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated
Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone.
Journal of Organic Chemistry (1994), 59(24), 7445-52.
Abe, Manabu; Oku, Akira.
Photoinduced electron transfer reaction of cyclopropanone acetals with
arylmethyl methanesulfonate: generation of -keto radical species and application
to C-C bond formation.
Journal of the Chemical Society, Chemical Communications (1994), (14),
1673-4.
Abe, Manabu; Oku, Akira.
Formation of unsaturated esters in the single electron transfer reaction
of cyclopropanone acetals with quinones under non-irradiation conditions.
Tetrahedron Letters (1994), 35(21), 3551-4.
Oku, Akira; Iwamoto, Masaharu; Sanada, Kenji; Abe, Manabu.
Ring-opening addition reaction of cyclopropanol derivatives with carbenes.
Tetrahedron Letters (1992), 33(47), 7169-72.
Oku, Akira; Urano, Shinichi; Nakaji, Toshiyuki; Qing, Ge; Abe, Manabu.
Bis(2-acetoxyacrylonitrile) and its phenylene and alkylene bis homologs.
Preparation, isomerization, and intramolecular [2 + 2] photocycloaddition.
Journal of Organic Chemistry (1992), 57(8), 2263-6.
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