Xanthateは熱分解によるオレフィン生成だけではなく,転位によって硫黄導入手段に使用できる
Allylic thiolおよびび allylic sulfideの合成
レトロエン反応の遷移状態
ジエノールキサンテートの三連続ペリ環状反応
研究に携わった方々は以下のとおりである.
三好浩一郎,大泉憲秀,三坂 恵祐,衛藤 仁,小野菊馬,西本光宏,上村 敏啓、久保田 昌嗣、清水範子, 藤井牧子,池田 千里、田尻 興保 ,山城 茂,芦村耕介,金城雄一,清永秀雄,横手千秋,濱田貴美子,秋葉悦子,寺田直子,頼藤 忍,溝口千秋
β-Cyclodextrin包接体における[3,3]-sigmatropy反応(不斉誘起) 清永秀雄,朝長 充則H8,古庄 晃H5,丸山 格H10,本多 教稔H11,秋吉 隆幸 H12,日高伸之介H14,多田隈景子 調査中
触媒による Xantahteの thion-thiol 転位に関する研究 篠原郁夫,村瀬元治,杉本慎一郎,野中美鈴,久保田昌嗣,中川秀稔
50. Catalytic Rearrangement of O-Cholesteryl S-Alkyl Dithiocarbonates to S-Alkyl S-Cholesteryl Dithiocarbonates by Phenols
K. Harano, K. Miyoshi and T. Hisano
Chem. Pharm. Bull., 1985, 33(5), 1861-1868). ⭕
52. A Convenient and Stereoselective Synthesis of Allylic Sulfides
K. Harano, N. Ohizumi and T. Hisano
Tetrahedron Lett., 1985, 26(35), 4203-4206.
58. Solvolytic Behavior of O-(1-Cycopropylethyl) S-Methyl Dithiocarbonate and Related Compounds
K. Harano, H. Kiyonaga and T. Hisano
Chem. Pharm. Bull., 1987, 35(4), 1388-1396. ⭕
59. Pyridine N-Oxides as Catalyst for Thione-Thiol Rearrangement
K. Harano, I. Shinohara, M. Murase and T. Hisano
Heterocycles, 1987, 26(10), 2583-2586.
60. 4-Dimethylaminopyridine N-Oxide as an Excellent Catalyst for Thione to Thiol Rearrangement of Xanthates
K. Harano, H. Kiyonaga, S. Sugimoto, T. Matsuoka and T. Hisano
Heterocycles, 1988, 27(10), 2327-2330.
62. Catalytic Rearrangement of O,S-Dialkyl Dithiocarbonates to S,S-Dithiocarbonates by Pyridine N-Oxides. The Reaction Mechanism
K. Harano, I. Shinihara, S. Sugimoto, T. Matsuoka and T. Hisano
Chem. Pharm. Bull., 1989, 37(3), 576-581. ⭕
66. Stereoselective Formation of Allylic Sulfide via Two Sequential [3,3]-Sigmatropic Rearrangements of Allylic Xanthates and Its Mechanistic Aspects
K. Harano, N. Ohizumi, K. Misaka, S. Yamashiro and T. Hisano
(1990 ・ Chem. Phram. Bull. ・ 38(3) ・ (619-624)). ⭕
68. Catalytic Behavior of Phenols in Pyrolytic Conversion of Allylic Dithiolcarbonates to Allylic Sulfides
K. Harano, S. Yamashiro, K. Misaka and T. Hisano
(1990 ・ Chem. Pharm. Bull. ・ 38(11) ・ (2956-2959)). ⭕
71. Linear Correlation of the Solvolysis Rates of Xanthates with the Grunwald-Winstein Y Values.
K. Harano, H. Kiyonaga, C. Yokote and T. Hisano
Chem. Pharm. Bull., 1991, 39(8), 1952-1957. ⭕
72. A Simple One-Pot Synthesis of Hydroisobenzothiophenes via Three-Step Sequential Pericyclic Reactions of Xanthates
K. Harano, K. Ono, M. Nishimoto, M. Eto and T. Hisano
Tetrahedron Lett., 1991, 32(21), 2387-2390.
73. [3,3]-Sigmatropic Rearrangement of Allylic Xanthates in β-Cyclodextrin Complexes
K. Harano, H. Kiyonaga and T. Hisano
Tetrahedron Lett., 1991, 32(51), 7557-7558.
76. Thione-Thiol Rearrangement of Xanthates Catalyzed by Pyridine N-Oxides. Remarkably Enhanced Reactivity of 4-Dialkylaminopyridne N-Oxides
K. Harano, H. Nakagawa, K. Kamei, H. Kiyonaga and T. Hisano
Chem. Pharm. Bull., 1992, 40(7), 1675-1682. ⭕
77. 4-Piperidinopyridine as an Effective Catalyst for Thione-Thiol Rearrangement of Xanthates
K. Harano, H. Nakagawa, H. Kiyonaga and T. Hisano
Org. Prep. Procd. Int., 1992, 24(2), 200-204.
80. Phenol-Catalyzed Thione-Thiol Rearrangement of Xanthates and MINDO/3 Analysis of the Reaction Mechanism
K. Harano, H. Kiyonaga and T. Hisano
Chem. Pharm. Bull., 1992, 40(10), 2654-2662. ⭕
84. An Improved Preparation of 2,4-Dinitrophenyl Thioethers from Thiolcarbonates
K. Harano, M. Eto, S. Kubota and T. Hisano
(1993 ・ Org. Prep. Proced. Int. ・ 25(1) ・ (130-133))
85. Sequential Pericyclic Reactions of Unsaturated Xanthates. One-Pot Synthesis of Hydroisobenzothiophenes
K. Harano, M. Eto, K. Ono, K. Misaka and T. Hisano
J. Chem. Soc. Perkin Trans. 1, 1993, 299-307.
95. Simple Synthesis of Furfuryl Sulfids via Extrusion of COS from the Xanthates and Its Mechanistic Aspects,
M. Eto, M. Nishimoto, T. Uemura, T. Hisano and K. Harano
J. Chem. Soc. Perkin Trans. 2, 1155-1162, 1995.
99. Retro-Ene Type Fragmentation of Allylic Dithiolcarbonates(AOX)
M. Eto, M. Nishimoto, S. Kubota, T. Matsuoka and K. Harano
Tetrahedron Lett., 1996, 37, 2445-2448.
謝辞 藤井牧子
101. Sequential Pericyclic Reaction of Unsaturated Xanthates. Intramolecular Cycloaddition Selectivity of the 2,4-Alkadienyl 2-Alkenyl Sulfides(AOX)
M. Eto, T. Uemura, N. Shimizu and K. Harano
Tetrahedron, 1996, 52, 13909-13918.
謝辞なし
109. Correlation of Thione-to-thiol Rearrangement Rates of Xanthates with Solvent Scales. Analysis of the Reaction Behavior by the Kamlet-Taft Parameters, π*, alpha and beta(Xan-Taft)
M. Eto, O. Tajiri, H. Nakagawa and K. Harano
Tetrahedron, 1998, 54, 8009-8014.
謝辞 池田 千里
110. Pyridine N-Oxide Catalyzed Thione-to-Thiol Rearrangement of Xanthates. MO Analysis of thr Reaction Mechanism (PyNO-Xan)
H. Nakagawa, M. Eto and K. Harano
Tetrahedron, 1998, 54, 9333-9340.
謝辞 なし
114. CATALYTIC THIONE-TO-THIOL REARRANGEMENT OF XANTHATES BY 4-DIALKYLAMINOPYRIDINE. MO ANALYSIS OF THE CATALYTIC BEHAVIOR (DAP-Xan)
H. Nakagawa, M. Eto and K. Harano
Heterocycles, 1999, 51, 51-59.
121. A X-ray Crystallographic and Computational Study of Intermolecular Edge-to-Face Aromatic Interaction in Crystal Structure of Exo [4+2]π Cycloadduct of Phencyclone and S-Allyl S-Methyl Dithiocarbonate(ASY CP DA 弱結合)
Yasuyuki Yoshitake, Hidetoshi Nakagawa, Masashi Eto and Kazunobu Harano
Tetrahedron, 2000, 56, 6015-6021.
123. Molecular Orbital Studies on Pericyclic Reactions of Cinnamyl Xanthates in b-Cyclodextrin Cavities(COX b-CyD MO)
Masashi Eto, Shoji Kubota, Hidetoshi Nakagawa, Yasuyuki Yoshitake and Kazunobu Harano
Chem. Pharm. Bull., 2000, 48(11), 1652-1659.
謝辞 朝長充則,溝口千秋
124. Theoretical Study of Neighboring-group Participation in Thione-to-Thiol Rearrangement of Xanthates. Molecular Orbital Calculations using Conductor like Screening (COSMO) Models (ROX MO COSMO)
Yasuyuki Yoshitake, Hidetoshi Nakagawa and Kazunobu Harano
Chem. Pharm. Bull., 2001, 49, 1433-1439. ⭕
134. A Cascade Reactions of Unsaturated Xanthates and Related Reactions: Computer-assisted Molecular Design and Analysis of Reaction Mechanisms
Kazunobu Harano
YAKUGAKU ZASSHI, 2005, 125(6), 469-489. ⭕
150. New Formation Mechanism of Allylic Trithiocarbonates from Sodium O-(2-Alkenyl) Dithiocarbonates via Sequential Pericyclic Reactions: Density Functional Theory Study
Masashi ETO, Koki YAMAGUCHI, Yasuyuki YOSHITAKE, Kazunobu HARANO*
Chem. Pharm. Bull., 2010, 58, 1517-1520. ⭕
151. Formation Mechanism of Furfuryl Sulfides from O-Furfuryl Dithiocarbonates: Density Functional Theory Study for Aromatic [3,3]-Sigmatropic Rearrangement
Masashi ETO, Koki YAMAGUCHI, Yasuyuki YOSHITAKE, Kazunobu HARANO*
Chem. Pharm. Bull., 2011, 59 (6), 681-685. ⭕
投稿論文番号150の図が,日本薬学会欧文誌 Chemical & Pharmaceutical Bulletinの表紙に採用された.
150. New Formation Mechanism of Allylic Trithiocarbonates from Sodium O-(2-Alkenyl) Dithiocarbonates via Sequential Pericyclic Reactions: Density Functional Theory Study
Masashi ETO, Koki YAMAGUCHI, Yasuyuki YOSHITAKE, Kazunobu HARANO*
Chem. Pharm. Bull., 2010, 58, 1517-1520.
衛藤 仁君の学位論文(PDF版を発見するのに時間がかかり,掲載が遅れました)
薬学雑誌に総説として掲載されたものです.