抄録
In this paper, the synthesis and properties of isopropyl-9-triptycylselenoketone 1a (iPrTrpC=Se) and cyclohexyl-9-triptycylselenoketone 1b (c-HexTrpC=Se) are reported as a novel type of carbon-selenium double bond compounds having an α-proton. The selenoketones 1a, b were isolated as green crystals and are not oxygen sensitive. Although the phenomenon of keto-enol type tautomerization has been known for such carbonyl compounds having α-protons, tautomerization of 1a, b to the corresponding eneselenol was not observed in solution. The oxidation of 1a, b with mCPBA gave the corresponding α,β-unstaturated selenenic acids (Trp(Me2C=)C-Se-OH and Trp((CH2)5C=)C-Se-OH) as the result of tautomerization of the selenines (iPrTrpC=Se=O and c-HexTrpC=Se=O). The reactivities of 1a, b as well as properties of the corresponding sulfur analogue will be discussed.
