69753-43-1

Upstream product

• 108-98-5 thiophenol 
• 69753-44-2 α,α-Bis(phenylthio)acetone 
• 22198-54-5 1-chloro-3-phenylsulfanylpropan-2-one 
• 64-19-7 acetic acid 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 2684-62-0 diazoacetone 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 22198-58-9 1-methoxy-1-phenylthiopropan-2-one 
• 87143-67-7 4,4-dimethyl-3-phenylthiohex-5-en-2-one 
• 344338-62-1 2-Methyl-2-(2-oxo-1-phenylsulfanyl-propyl)-cyclohexanone 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 77128-60-0 3-Methyl-2-phenylsulfanyl-benzo[b]thiophene 
• 77128-53-1 (2R,3R)-3-Methyl-2-phenylsulfanyl-2,3-dihydro-benzo[b]thiophen-3-ol 
• 882-33-7 diphenyldisulfane 
• 10371-49-0 1-phenyl-1-(phenylthio)-2-propenone 
• 65755-66-0 3-phenylthiohex-5-ene-2-one 
• 113502-94-6 2-Methyl-3-phenylsulfanyl-naphtho[2,3-b]furan 
• 344306-21-4 2-(2-Oxo-1-phenylsulfanyl-propyl)-cyclopentanone 
• 87143-64-4 3-Phenylsulfanyl-4-vinyl-nonan-2-one 
• 22198-56-7 1-acetoxy-1-phenylthio-2-propanone 
• 22198-57-8 acetate of 1-hydroxy-3-phenylthio-2-propanone 

Relevant academic research and scientific papers

Cationic Polar Cycloadditions of Phenylthionium Ions with Olefines: A New Route to Thiochromans

Reaction of 2-chloro-N,N-dimethyl-2-(phenylthio)acetamide (1a) with styrene in the presence of stannic chloride gave 3,4-dihydro-N,N-dimethyl-4-phenyl-2H-1-benzothiopyran-2-carboxamide.The same benzothiopyran was also obtained from N,N-dimethyl-2-(phenylsulfinyl)acetamide and styrene under the Pummerer reaction conditions, but in lower yield.Similarly, α-chlorosulfides derived from ethyl 2-(phenylthio)acetate, 2-(phenylthio)acetonitrile, 1-(phenylthio)-2-propanone, and thioanisole reacted with styrene to give the corresponding 4-phenylbenzothiopyrans in variable yields.The reaction of 1a with trans-stilbene gave the expected benzothiopyran derivative, but the reaction of 1a with 1,1-diphenylethylene and phenylacetylene showed some variation of the reaction course.This cycloaddition reaction was extended to the intramolecular case.A possible mechanism for the formation of the benzothiopyran is discussed.

NUCLEOPHILIC SUBSTITUTION OF α-HALO-KETONES-XXII ACETOLYSIS OF α'-PHENOXY-α-CHLORO-KETONES. A COMPARISON OF THEIR REACTIVITY WITH THAT OF THE CORRESPONDING THIOETHERS

The results obtained in the acetolysis of α-chloro-ketones 1 a-e are compared with those previously reported for the acetolysis of the corresponding α'-phenylthio-α-chloro-ketones 15a-e and discussed in terms of the enolization-solvolysis mechanisms.

REGIOSPECIFIC SYNTHESIS OF α-(PHENYLTHIO)CYCLOALKENONES AND OF α-PHENYL-α-(PHENYLTHIO)KETONES VIA αα-ADDITION OF PHENYLSULPHENYL CHLORIDE TO α-DIAZOKETONES

Cyclic α-diazoketones react with phenylsulphenyl chloride at room temperature to furnish α-chloro-α-(phenylthio)cycloalkanones which undergo ready dehydrochlorination to α-(phenylthio)cycloalkenones when treated with triethylamine; acyclic, terminal α-diazoketones also furnish α-chloro-α-(phenylthio)adducts which are useful electrophiles in the synthesis of α-phenyl-α-(phenylthio)ketones.

PHOTOCHEMICAL RING CLOSURE OF α,α-BISULFENYLATED CARBONYL COMPOUNDS STEREOSELECTIVE FORMATION OF CIS-DIHYDROBENZOTHIOPHENES

Photochemistry of α,α-bisulfenylated ketone has been investigated.Irradiation of 2-phenylthiodihydrothiophen-3-one (1) in benzene gave the radical recombination products 9 (63percent) and 10 (49percent).In a polar solvent, the ionic chemistry became predominant.Brief irradiation of 1 in acetonitrile and methanol gave the cis-fused dihydrothiophene 11 as the major product in 43percent and 20percent yields, respectively.The stereoselective photocyclization was generally observed for other ketones (2-8) in acetonitrile solution (Table 1).The photoproducts were easily dehydrated by treating with boron trifluoride etherate to give the corresponding benzothiophenes in high yields.Simple α-phenylthioketones are photoinert under the same conditions.The mechanism of this novel photocyclization of bisulfenylated ketones is also discussed.

NUCLEOPHILIC SUBSTITUTION OF α-HALO KETONES. XXI. STRUCTURE-REACTIVITY RELATIONSHIPS IN THE ACETOLYSIS OF 3-SUBSTITUTED 1-CHLORO-3-PHENYLTHIO-2-PROPANONES

The acetolyses of α-chloro ketones 1a-d have been re-investigated under standard conditions and compared with those of the corresponding isomeric substrates 2a-d.It has been shown that participation by the neighbouring phenylthio group, involving a 1-3 shift of the latter, does occur in part even in the case of 1d, while it is the only process in the case of 1e.A few structure-reactivity relationships in the two series of substrates are discussed.

α-CETOALDEHYDES A GROUPEMENT ALDEHYDIQUE OU CETONIQUE PROTEGE

α-Ketoaldehydes with protected ketogroup 2 or protected aldehydrogroup 3 are obtained by reaction of thiophenol or methanol with α-chloro-α-(phenylthio)aldehydes 7.