35809-27-9

Upstream product

• 35116-16-6 2-chloro-heptanal 
• 930-69-8 sodium thiophenolate 
• 17510-50-8 1-trimethylsilanyloxy-hept-1-ene 
• 931-59-9 benzenesulfenyl chloride 
• 16486-84-3 2-bromoheptanal 
• 108-98-5 thiophenol 
• 84980-54-1 2-phenylthioheptanal tosylhydrazone 
• 111-71-7 heptanal 
• 14204-27-4 N-phenylthiophthalimide 
• 52718-79-3 n-Heptaldehyd-tosylhydrazon 
• 628-71-7 1-Heptyne 

Downstream Products

• 77331-02-3 2-Chloro-2-phenylsulfanyl-heptanal 
• 1246593-15-6 ethyl (E)-4-(phenylthio)non-2-enoate 
• 1246593-30-5 ethyl (Z)-4-(phenylthio)non-2-enoate 
• 77331-05-6 2,2-Bis-phenylsulfanyl-heptanal 
• 77331-10-3 (Z)-2-Phenylsulfanyl-hept-2-enal 

Relevant academic research and scientific papers

Air Oxidative Radical Oxysulfurization of Alkynes Leading to α-Thioaldehydes

Air oxidative radical oxysulfurization of alkynes initiated by 0.5 mol % tert-butyl hydroperoxide with arylthiols is described. The reaction proceeded at room temperature in the presence of 5% mol water to afford selective α-thioaldehydes. (Chemical Equation Presented).

Exopericyclic stereocontrol in Johnson-Claisen rearrangements of allylic sulfides

A study of the effects of exopericyclic stereocentres on the stereoselectivity of Johnson-Claisen rearrangements of thioether-containing allylic alcohols shows that selectivity is highly dependent upon allylic substitution patterns.

ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS

The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo--selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R", NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ("hydrocarbyl") group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R" are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R" form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R" are attached; and wherein said compound is free from a metal catalyst.

Direct, organocatalytic α-sulfenylation of aldehydes and ketones

A method for direct sulfenylation of aldehydes and ketones, catalyzed by a novel pyrrolidine trifluoromethanesulfonamide organocatalyst, has been developed. This process serves as an efficient and mild approach to the preparation of α-phenylthio-ketones and -aldehydes.

Conversion of Tosylhydrazones of α-Halogeno-aldehydes and -ketones into the Corresponding Phenylthio- and Phenylseleno-derivatives

The tosylhydrazones of 2-chlorocyclohexanone, 2-chlorocyclopentanone, 1-chloropropanone, phenacyl chloride, 2-bromoheptanal and 2-bromo-2-methylpropanal (1), (5a),(7a),(8b), and (9b), respectively, reacted rapidly with thiophenol and an excess of triethylamine in tetrahydrofuran at -78 deg C to give the corresponding α-phenylthio-substituted tosylhydrazones (3a), (5b), (7b), (8c), and (9c) in good yields.The α-phenylseleno-substituted tosylhydrazones (3b),(5c), (6c), (8d), and (9d) were similarly prepared, in satisfactory yields, by treating the corresponding α-halogeno-substituted tosylhydrazones with benzeneselenol and an excess of triethylamine.Several α-phenylthio-substituted carbonyl compounds and 2-phenylselenocyclohexanone (4b) were regenerated from the corresponding tosylhydrazones in good yields.

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.