30456-90-7

Basic information

• Product Name: 1,3,5-Cycloheptatriene-7-thione
• Synonyms: 1,3,5-Cycloheptatriene-7-thione;2,4,6-Cycloheptatriene-1-thione;Tropothione
• CAS NO: 30456-90-7
• Molecular Formula: C₇H₆S
• Molecular Weight: 122.19
• Mol File: 30456-90-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3,5-Cycloheptatriene-7-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Cycloheptatriene-7-thione(30456-90-7)
• EPA Substance Registry System: 1,3,5-Cycloheptatriene-7-thione(30456-90-7)

Safety Data

• Hazardous Substances Data: 30456-90-7(Hazardous Substances Data)

Upstream product

• 539-80-0 Tropone 
• 259-69-8 (5aS,11aS)-5aH,11aH-6,12-Dithia-benzo[1,2;4,5]dicycloheptene 

Downstream Products

• 61059-28-7 3,3-Diphenyl-3,3a-dihydro-cyclohepta[b]thiophen-2-one 
• 539-80-0 Tropone 

Relevant articles and documents

Synthesis and Isolation of Tropothione: A Comparative Study of Spectral Property with Tropone

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 1/2(crystalline state, 0 deg C) 56 min>, dilute solutions are found to be sufficiently stable enough for measuring spectral data 1/2(0.01 mol/L, 25 deg C) 10.4 days>.The compound 1 is isolated as a labile material of deep red crystals with the melting range of 20-21 deg C.IR spectrum of 1 exhibits a very strong band of the νC=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-?* 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.

Inverting the reactivity of troponoid systems in enantioselective higher-order cycloaddition

By the replacement of the oxygen with the sulfur atom in tropone, a novel reactivity pattern of troponoid systems in enantioselective transformation was achieved. It utilizes tropothione as an 8π-component in the [8+2]-cycloaddition involving α,β-unsaturated aldehydes. The stereochemistry of the process is governed through the aminocatalytic LUMO-activation of the carbonyl reactant. It is in marked contrast to recently developed aminocatalytic higher-order cycloadditions proceeding via HOMO-activation strategies.