Chemistry of thermally stable monosubstituted thiophene S-oxide and related compounds
| Project/Area Number |
25410055
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Anan National College of Technology (2015)
Tokyo University of Science (2013-2014) |
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Principal Investigator |
Otani Takashi 阿南工業高等専門学校, その他部局等, 講師 (70339109)
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| Co-Investigator(Renkei-kenkyūsha) |
SHIBATA Takanori 早稲田大学, 理工学部, 教授 (80265735)
MATSUO Tsukasa 近畿大学, 理工学部, 准教授 (90312800)
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| Project Period (FY) |
2013-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | チオフェン / 芳香族性 / 有機硫黄化学 / チオフェン１ーオキシド / チオフェン１ーイミド / オリゴチオフェン / チオフェン 1-オキシド / チオフェン 1-イミド |
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| Outline of Final Research Achievements |
Thiophene S-oxide does not possess sufficient electron density for aromatization and thus readily dimerize in a [4+2] (Diels-Alder) manner. Introduction of two substituents on the thiophene ring has been required for their kinetic and/or thermodynamic stabilization for nearly a half century.
We have succeeded in the synthesis and characterization of thermally stable monosubstituted thiophene S-oxide and S-imides stabilized by EMind (1,1,7,7-tetraethyl-3,3,5,5-tetramethyl-s-hydrindacen-4-yl) group on the 3-position. In addition to the molecular structures determined by X-ray crystallography, inversion barriers at the three-coordinated sulfur atoms have been determined by a coalescence method using diastereotopic C-3 and C-5 indacene carbon atoms as a 13C-NMR probe.
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Report
(4 results)
Research Products
(20 results)
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[Journal Article] [3]-1-Azadendralenes as versatile building blocks for stereoselective synthesis of polysubstituted hexahydroquinazolin-2-ones and hexahydrobenzothiazine-2-imines2015
Author(s)
Satoru Kobayashi, Kenji Kudo, Ai Ito, Takuya Honjo, Masahiro Yata, Takashi Otani, Noriki Kutsumura, Takao Saito, Fabienne Berree, Elise Romain, Fabien Tripoteau and Bertrand Carboni
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Journal Title
European Journal of Organic Chemistry
Volume: 2015
Issue: 20
Pages: 4367-4373
DOI
Related Report
Peer Reviewed / Int'l Joint Research
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[Journal Article] Intramolecular [2+2+2] cycloaddition of bis(propargylphenyl)carbodiimides: synthesis of L-shaped π-extended compounds with pyrrolo[1,2-a][1,8]naphthyridine corner units2013
Author(s)
T. Otani, T. Saito, R. Sakamoto, H. Osada, A. Hirahara, N. Furukawa, N. Kutsumura, T. Matsuo, K. Tamao
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Journal Title
Chem. Commun.
Volume: 49
Issue: 55
Pages: 6206-6208
DOI
Related Report
Peer Reviewed
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