Chemistry of thermally stable monosubstituted thiophene S-oxide and related compounds

2015 Fiscal Year Final Research Report

• Project/Area Number: 25410055
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Anan National College of Technology (2015); Tokyo University of Science (2013-2014)
• Principal Investigator: Otani Takashi 阿南工業高等専門学校, その他部局等, 講師 (70339109)
• 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)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: チオフェン / 芳香族性 / 有機硫黄化学

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.

Free Research Field

有機合成化学