34804-73-4

Upstream product

• 2548-47-2 2,3-diphenyl-1,3-butadiene 
• 108617-86-3 dithiatopazine 
• 116195-00-7 9,10-dihydro-9,10-(1,3-epidithio-2-methano-2-p-methoxyphenyl-1-oxide)-propanoanthracene 
• 110027-90-2 5,5-Dimethyl-1,2-dithia-3,7-diselenacycloheptan 
• 6363-17-3 (Z)-(1,4-dibromobut-2-ene-2,3-diyl)dibenzene 
• 180316-20-5 5--4-chloro-5H-1,2,3-dithiazole 
• 76048-12-9 O,O-Bicyclohexyl-1,1'-diyl thiosulphite 
• 98-81-7 1-bromovinylbenzene 
• 62142-84-1 (Z)-2,3-diphenyl-2-butene-1,4-diol 
• 113495-60-6 2,5-dihydro-3,4-diphenylselenophene 
• 39167-49-2 1,5-diphenyl-3-selena-1,5-pentanedione 
• 1258522-84-7 4,5-diphenyl-3,6-dihydrodiselenin 
• 4808-48-4 2,3-diphenylmaleic anhydride 
• 5635-16-5 3,4-diphenyl-2(5H)-furanone 

Downstream Products

• 34826-14-7 4,5-diphenyl-3,6-dihydro-1,2-dithiine 1-oxide 
• 16939-13-2 3,4-diphenylthiophene 
• 100989-94-4 3-(2-chlorophenyl)-4-phenylthiophene 
• 22875-84-9 2,3-diphenyl-1-butene 
• 34804-74-5 6,7-Diphenyl-5,8-dihydro-1,2,3,4-tetrathiocin 

Relevant academic research and scientific papers

The sulfur diatomics: Generation and trapping chemistry

Aspects of the generation and trapping of diatomic sulfur (S2) and sulfur monoxide (SO) are reviewed with special emphasis on recent work.

Sulfur allotrope chemistry - S10 an effective two-sulfur transfer reagent

The chemistry of one of the sulfur allotropes has been investigated. Cyclodecasulfur (S10) reacts with conjugated 1,3-dienes and strained olefins to deliver cyclic di- and polysulfides with a better selectivity and under milder conditions than with elemental sulfur (S8). A radical mechanism is proposed for these sulfuration reactions.

Catalytic sulfuration of dienes with metallocene polysulfides

Elemental sulfur reacts with conjugated 1,3-dienes to give cyclic di- and tetrasulfides. The yield is significantly improved in the presence of catalytic amounts of organometallic polysulfides. The nature of this effect is discussed.

Quest for diatomic selenium

Metallocene pentaselenides and elemental selenium were employed in an effort to generate diatomic selenium (Se2) under thermal conditions. Trapping experiments were carried out with six dienes. A successful formation of a diselenium adduct was observed in the case of 5,6-dimethylene-cyclohexa-1,3- diene (1a). The other dienes produced the corresponding dihydroselenophenes. The in-depth study of the limitations of our method to generate Se2 is described; a plausible mechanism rationalizing the observed results is proposed.

Diselenide-assisted sulfuration of dienes

Various diselenides assist in the sulfuration of dienes giving cyclic di- and tetrasulfides as main products. The reaction requires a 2-fold excess of diselenides to be efficient. Catalytic amounts of diselenides result in lower yields. This is likely due to secondary reactions (polymerization, aromatization) occurring during extended reaction times under catalytic conditions. It was verified that the sulfur-transferring properties of diselenatetrasulfides are virtually identical to those of diselenides combined with sulfur. Contrary to previous claims, not only the cyclic diselenatetrasulfide but also linear diselenatetrasulfides (RSeSnSeR) transfer sulfur to dienes. A mechanism is proposed and its implications to the nature of diatomic sulfur are discussed.

Dialkoxy disulfides from cubycarbinols

Two dialkoxy disulfides 2 and 3 have been synthesized in respectable yields. The behaviour of 2 and 3 under thermal and photolytic conditions has been examined and we report the first examples of S2 liberation from aliphatic dialkoxy disulfides.

New route to 2-cyanobenzimidazoles

N-Monosubstituted 1,2-diaminobenzenes 4 (R = Me, Ph, PhCH2, and 3,4- Me2C6H3CH2) react with 4,5-dichloro-1,2,3-dithiazolium chloride 1 in dichloromethane at room temperature to give the corresponding 2- cyanobenzimidazoles 6. If pyridine is added at the beginning of the reaction, the intermediate imino-1,2,3-dithiazoles 5 can be isolated. Upon thermolysis, most of the imines 5 give the 2-cyanobenzimidazoles 6 in fair to good yields. 1.2-Diaminobenzene can be converted in high yield into the mono-imine 5i or the bis-imine 12, R = H; thermolysis of 5i gives 2-cyanobenzimidazole in high yield. Conversion of 5 into 6 involves the loss of both sulfur atoms and with the N-phenylimino derivative 5b singlet diatomic sulfur, S2, has been intercepted with norbornene and with 2.3-diphenylbutadiene to give the expected cycloadducts 7 and 8.

Sulfuration of dienes with elemental sulfur

Elemental sulfur reacts with conjugated 1,3-dienes to deliver cyclic di- and polysulfides; the reaction proceeds without any activation other than heat. Treatment of cyclic polysulfide products with triphenylphosphine cleanly converts them to the corresponding disulfide in good overall yield. Additionally, some mechanistic aspects have been examined. The presence of disulfur as an active species in the sulfuration of dienes with S8 is discussed.

Recent chemistry of the chalcogen diatomics

The chemistry of the generation and trapping of diatomic sulfur (S2) and sulfur monoxide (SO) are reviewed with special emphasis on recent work, including initial efforts to detect and trap diatomic selenium (Se2).

Conversion of imino-1,2,3-dithiazoles into 2-cyanobenzothiazoles, cyanoimidoyl chlorides and diatomic sulfur

Primary aromatic amines condense with 4,5-dichloro-1,2,3-dithiazolium chloride 1 to give high yields of the N-aryl imines 2 which on heating give 2-cyanobenzothiazoles 3, thus providing a simple two-step route to these heterocycles from the appropriate aniline. This thermolysis is favoured by electron donating substituents in the aniline ring, and retarded by electron withdrawing groups in favour of a second pathway in which both dithiazole sulfur atoms are lost to form cyanoimidoyl chlorides 4. This is the sole pathway when both aniline ortho positions are substituted. Analogous N-alkyl imines 5, prepared from the salt 1 and the bis(trimethylsilyl) derivatives of the amine, also decompose with loss of both sulfur atoms as singlet diatomic sulfur, S2. 4-Chloro-5-methylimino-5H-1,2,3-diathiazole 5a does this at 140-150°C and the S2 generated is intercepted with 2,3-diphenylbutadiene, 2,3-dimethylbutadiene and norbornene to give 16a, 16b and 17 respectively.