34826-14-7

Basic information

• Product Name: 4,5-diphenyl-3,6-dihydro-1,2-dithiine 1-oxide
• Synonyms: 4,5-Diphenyl-3,6-dihydro-1,2-dithiine 1-oxide
• CAS NO: 34826-14-7
• Molecular Formula: C₁₆H₁₄OS₂
• Molecular Weight: 286.4118
• Mol File: 34826-14-7.mol

Chemical Properties

• Boiling Point: 484.5°C at 760 mmHg
• Flash Point: 246.8°C
• Density: 1.33g/cm³
• Vapor Pressure: 4.53E-09mmHg at 25°C
• Refractive Index: 1.714
• CAS DataBase Reference: 4,5-diphenyl-3,6-dihydro-1,2-dithiine 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-diphenyl-3,6-dihydro-1,2-dithiine 1-oxide(34826-14-7)
• EPA Substance Registry System: 4,5-diphenyl-3,6-dihydro-1,2-dithiine 1-oxide(34826-14-7)

Safety Data

• Hazardous Substances Data: 34826-14-7(Hazardous Substances Data)

Upstream product

• 2548-47-2 2,3-diphenyl-1,3-butadiene 
• 98-81-7 1-bromovinylbenzene 
• 62142-84-1 (Z)-2,3-diphenyl-2-butene-1,4-diol 
• 6363-17-3 (Z)-(1,4-dibromobut-2-ene-2,3-diyl)dibenzene 
• 4808-48-4 2,3-diphenylmaleic anhydride 
• 5635-16-5 3,4-diphenyl-2(5H)-furanone 
• 67300-99-6 1-phenylethenylmagnesium bromide 
• 34804-73-4 4,5-diphenyl-3,6-dihydro-1,2-dithiin 

Downstream Products

• 2548-47-2 2,3-diphenyl-1,3-butadiene 
• 56391-52-7 (C₂H₄(P(C₆H₅)2)2)2IrS₂O⁽¹⁺⁾*Cl^(1-)=(C₂H₄(P(C₆H₅)2)2)2IrS₂OCl 
• 586960-37-4 cyclopentadienyl(1-oxo-5-(4'-trifluoromethylphenyl)-1,2-dithiol-4-enyl)dicarbonyliron 
• 586960-36-3 cyclopentadienyl(1-oxo-5-(4'-acetylphenyl)-1,2-dithiol-4-enyl)dicarbonyliron 
• 586960-38-5 cyclopentadienyl(1-oxo-5-(4'-methoxyphenyl)-1,2-dithiol-4-enyl)dicarbonyliron 
• 218956-25-3 ((CH₃)2C₆H₅P)(CO)4Mn(S₂OCH₂C(CH₃)CH₂) 
• 218956-24-2 ((CH₃)2C₆H₅P)(CO)4Mn(S₂OCH₂CHCH₂) 

Relevant articles and documents

Reversible disulfur monoxide (S2O)-forming retro-Diels-Alder reaction. Disproportionation of S2O to trithio-ozone (S3) and sulfur dioxide (SO2) and reactivities of S2O and S3

5,6-Di-tert-buty(-2,3,7-trithiabicyclo[2.2.1]hept-5-ene 7-endo-oxide (4) was prepared by addition of S2Cl2 to 3,4-di-tert- butylthiophene 1-oxide (3) in high yield. The oxidation of 4 with dimethyldioxirane gave a 7:1 isomeric mixture of 5,6-di-tert-butyl-2,3,7- trithiabicyclo[2.2.1]hept-5-ene 2-endo-7-endo-dioxide (5a) and 2-exo-7-endo-dioxide (5b) quantitatively. The thermally labile 5 was shown to undergo a retro-Diels-Alder reaction that produces S2O and 3 in a reversible way. The resulting S2O was trapped by Diels-Alder reactions with dienes to give 3,6-dihydro-1,2-dithiin 1 -oxides in good yields. In the absence of the dienes, S2O disproportionates to SO2 and S3, and the resulting S3 underwent a 1,3-dipolar cycloaddition with 3 on its syn-π-face with respect to the S=O bond to give a trithiolane derivative, whereas in the presence of excess norbornene, it produced the 1,3-dipolar cycloadduct with norbornene in good yield. Thus, the retro-Diels-Alder reaction of 5 functions as an S2O and S3 source. DFT calculations at the B3LYP/6-311+G(3df,2p) level were carried out in order to explain why S2O disproportionates to SO2 and S3 and why S2O acts as a dienophile and not 1,3-dipole, whereas O3 and S3 serve as 1,3-dipoles.

A convenient method for the generation of a disulfur monoxide equivalent and its reaction with diazoalkanes to yield dithiirane 1-oxides

Oxidation of elemental sulfur (S8) with dimethyldioxirane (or CF3CO3H) generates a disulfur monoxide equivalent ("S2O"). Yields of "S2O" of 30-40% are obtained from equimolar amounts of S8 and an oxidizing agent. "S2O" reacts with diazoalkanes to give dithiirane 1-oxides [Eq. (1)].

A simple synthesis of the S2O source, 4,5-diphenyl-1,2-dithiin-1-oxide

An improved procedure for the synthesis of 2,3-diphenyl-1,3-butadiene is reported along with its utilization in a simple synthesis of the S2O precursor, 4,5-diphenyl-1,2-dithiin-1-oxide.

Investigation of a transition metal-assisted retro Diels-Alder reaction used in the synthesis of transition metal S2O complexes

Treatment of 4,5-diphenyl-3,6-dihydro-1,2-dithiin-1-oxide with coordinatively unsaturated transition metal complexes resulted in the production of S2O complexes and 2,3-diphenylbutadiene.A transition metal-assisted retro Diels-Alder mechanism has been proposed for this reaction.A series of IR and 1H NMR experiments and MNDO calculations on 4,5-diphenyl-3,6-dihydro-1,2-dithiin-1-oxide have been performed to gain additional information about this transformation.