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• W2045889352 abstract "The synthesis, isolation, and spectral characterization of tropothione (1), the sulfur analogue of tropone (2), are described with comparison of those for 2. Direct sulfurization of 2 with tetraphosphorous decasulfide using triethylamine as a catalyst yields the titled compound 1 in high yield. Although 1 is thermally unstable material [t12 (crystalline state, 0 °C) 56 min], dilute solutions are found to be sufficiently stable enough for measuring spectral data [t12 (0.01 mol/L, 25 °C) 10.4 days]. The compound 1 is isolated as a labile material of deep red crystals with the melting range of 20–21 °C. IR spectrum of 1 exhibits a very strong band of the vC=S stretching vibration at 1087 cm−1 in CCl4. Raman spectrum supports the assignment. UV-visible spectra in six solvents show three transitions at around 225 (log ε ca. 4), 253 (ca. 4), and 380 nm (ca. 4.2), while 1 exhibits an additional weak absorption of n−π∗ transitions at 610 nm (log ε 1.62). 1H NMR of 1 shows wide signals of symmetrical AA′BB′XX′ pattern comprising with a large downfield part of α-protons in the ring due to the magnetic anisotropy of the CS group greater than that of CO one in 2. 13C NMR of 1 displays three doublet signals (δ 131.48, 138.36, and 153.80) accompanying with the singlet one at δ 213.83 (C=S). 33S NMR of 1 exhibits δ − 287 as the first measurement for thiocarbonyl compounds. These physical properties of 1 are in sharp contrast to those of 2." @default.
• W2045889352 created "2016-06-24" @default.
• W2045889352 creator A5028675300 @default.
• W2045889352 date "1995-01-01" @default.
• W2045889352 modified "2023-10-17" @default.
• W2045889352 title "Synthesis and isolation of tropothione: A comparative study of spectral property with tropone" @default.
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• W2045889352 doi "https://doi.org/10.1016/0040-4020(94)01001-g" @default.
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