163926-75-8

Basic information

• Product Name: 2-p-tolylnaphtho<1,8-de>-1,3-dithiin
• Synonyms: 2-p-tolylnaphtho<1,8-de>-1,3-dithiin
• CAS NO: 163926-75-8
• Molecular Weight: 294.441
• Mol File: 163926-75-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-p-tolylnaphtho<1,8-de>-1,3-dithiin(CAS DataBase Reference)
• NIST Chemistry Reference: 2-p-tolylnaphtho<1,8-de>-1,3-dithiin(163926-75-8)
• EPA Substance Registry System: 2-p-tolylnaphtho<1,8-de>-1,3-dithiin(163926-75-8)

Safety Data

• Hazardous Substances Data: 163926-75-8(Hazardous Substances Data)

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 209-22-3 1,8-naphthalenedisulfide 
• 25079-77-0 naphthalene-1,8-dithiol 
• 163926-76-9 2-Ethyl-naphtho[1,8-de][1,3]dithiine 
• 156462-93-0 2-Hexyl-naphtho[1,8-de][1,3]dithiine 
• 156462-95-2 2-(2-furyl)naphtho<1,8-de>-1,3-dithiin 
• 156462-94-1 2-((E)-Styryl)-naphtho[1,8-de][1,3]dithiine 
• 163926-85-0 N-[2-Ethyl-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-4-methyl-benzenesulfonamide 
• 163926-83-8 1-phenyl-naphtho<1,8-de>1,3-dithiane-1-N-tosylsulfilimine 
• 163926-88-3 N-[2-Furan-2-yl-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-4-methyl-benzenesulfonamide 
• 163926-86-1 N-[2-Hexyl-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-4-methyl-benzenesulfonamide 
• 163926-87-2 4-Methyl-N-[2-((E)-styryl)-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-benzenesulfonamide 

Downstream Products

• 156462-92-9 2-phenylnaphtho<1,8-de><1,3>dithiin 
• 156462-94-1 2-((E)-Styryl)-naphtho[1,8-de][1,3]dithiine 
• 163926-85-0 N-[2-Ethyl-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-4-methyl-benzenesulfonamide 
• 163926-86-1 N-[2-Hexyl-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-4-methyl-benzenesulfonamide 
• 163926-87-2 4-Methyl-N-[2-((E)-styryl)-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-benzenesulfonamide 
• 14111-33-2 diethyl 2-(4-methylbenzylidene)malonate 
• 181023-30-3 9-p-Tolyl-7,10-dithia-cyclohepta[de]naphthalene-8,8-dicarboxylic acid diethyl ester 
• 163926-84-9 4-Methyl-N-[2-p-tolyl-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-benzenesulfonamide 

Relevant articles and documents

Evidence of transannular bonding interaction between two sulfur atoms on photolysis of naphtho[1,8-ef][1,4]dithiepins

Naphtho[1,8-ef][1,4]dithiepins 5 were prepared by the reaction of naphtho[1,8-de]-1,3-dithiins 3 with diethyl diazomalonate in the presence of copper acetylacetonate. The X-ray crystallographic analysis of 2,3-dihydro-2,2-bis(ethoxycarbonyl)-3-phenylnaphtho[1,8-ef][1,4]dithie pin (5a) revealed that the S···S distance is shorter than the sum of their van der Waals radii, indicating that compounds 5 have a strong through-space interaction between the two sulfur atoms. Direct irradiation of 5 with a 500 W high-pressure mercury lamp (313 nm) at room temperature gave the corresponding olefins 6 and naphtho[1,8-cd]-1,2-dithiole (1) quantitatively. The quantum yields of the consumption of 5a and the formation of 6a and 1 were 0.34. The mechanism of this reaction was investigated by examining the effect of sensitization and light intensity. The results indicate that the reaction may proceed by a one-photon process from an excited singlet state. Ab initio calculations were carried out on model compound 7, and it was shown that the excitation to the S1 state causes a bonding interaction between the two sulfur atoms, making the reaction possible.

Mechanism for photodecomposition of naphtho[1,8-de][1,3] dithiin-1-bis(ethoxycarbonyl)methylides

Naphtho[1,8-de][1,3]dithiin-1-bis(ethoxycarbonyl)methylides (3) were prepared by the reaction of naphtho[1,8-de]dithiins with diethyl diazomalonate in the presence of copper acetylacetonate. The sulfonium ylides 3 underwent photo-rearrangement giving olefin 5 quantitatively together with naphthalene-1,8-dithiole.