71638-76-1

Upstream product

• 504-61-0 (E)-but-2-enol 
• 86971-24-6 2-(benzylthio)benzo[d]oxazole 
• 563-52-0 2-chloro-3-butene 
• 109384-47-6 S-Benzyl S-(1-methylallyl) dithiocarbonate 
• 100-39-0 benzyl bromide 
• 188400-13-7 S-(E)-crotyl N-methylthiocarbamate 
• 142108-97-2 Dithiocarbonic acid S-benzyl ester O-((E)-but-2-enyl) ester 
• 100-53-8 phenylmethanethiol 
• 598-32-3 2-hydroxy-3-butene 
• 6117-91-5 (E/Z)-2-buten-1-ol 
• 142108-97-2 O-crotyl S-benzyl dithiocarbonate 
• 100-44-7 benzyl chloride 
• 109384-48-7 Dithiocarbonic acid S-benzyl ester S-((E)-but-2-enyl) ester 

Relevant academic research and scientific papers

Method of manufacturing compds. Allylnaphthol

PROBLEM TO BE SOLVED: To provide a production method of an allyl compound of carrying out the dehydration allylation of a substrate having S, C or N which is a nucleophilic atom, especially S under the presence of a catalyst system consisting of a catalyst precursor having a specific structure and a specific ligand. SOLUTION: The production method of allyl compounds comprises as follow. A catalyst precursor chosen from Formula (1) and Formula (2) and a ligand are mixed, or a catalyst precursor, an allyl alcohol, and a ligand are mixed, then allyl alcohols and a substrate are blended and made to react. The ligand is quinaldic acid or picolinic acid, and the substrate is thiols, thiocarboxylic acids or the like. [Ru(C5H5)(CH3CN)3]PF6(1). [Ru[C5(CH3)5](CH3CN)3]PF6(2). COPYRIGHT: (C)2012,JPOandINPIT

Highly efficient catalytic dehydrative S-allylation of thiols and thioic S-acids

A SH-selective allylation method using [CpRu(2-quinolinecarboxylato) (η3-C3H5)]PF6 has been realized in various solvents including aqueous media to give allyl sulfides and allyl S-thioates, demonstrating the potential applicability to lipopeptide chemistry.

Aromatic Allylsulfenylation with in Situ Generated Allylic Thiols under the Heck Conditions

A wide structural variety of S-allylic thiocarbamates 2 can be prepared in good yields by the rearrangement of O-allylic thiocarbamates 1 under three different conditions: thermal activation (neat, 120-150°C), palladium(0) (25-65 °C), and palladium(II) catalysis (25-65°C). Of the two possible regioisomers of unsymmetrical S-allylic thiocarbamates 2, those of higher thermodynamic stability can be prepared in high purity under either thermal activation or palladium(0) catalysis. Although the thermodynamically less stable regioisomers of 2 are, in general, hard to be prepared in high purity, some of them (e.g., 2d and 2h′) can be obtained with an exclusive or high selectivity by the catalysis of palladium(II). The stereoisomeric pair of 2j and 2j′ can be prepared selectively by the palladium(0)-catalyzed rearrangement of 1j and 1k, respectively. These reactions proceed with retention of configuration at the allylic stereocenters, S-Allylic (2) and S-alkyl thiocarbamates (7) undergo fragmentation to generate thiolates in the presence of inorganic bases (e.g., K2CO3, K2CO3·-Et4N+I-) by heating in an aprotic solvent; the thus-formed thiolates react with aromatic iodides and vinyl bromides in the presence of palladium(0) complexes to furnish aryl and vinyl sulfides, respectively. A wide variety of aryl sulfides can be prepared in good yields irrespective of the kind of substituents and their substitution positions (o-, m-, p-) under conditions B [Pd(OAc)2, PPh3, K2CO3·Et4N+I-, dioxane, 100°C]. Under conditions E [Pd(OAc)2, PPh3, Cs2CO3, dioxane, 100°C], better yields result specifically for the sulfenylation of aromatic iodides bearing substituents having large Hammett σ constants.

Aromatic allylsulfenylation with in situ generated allyl thiols under the Heck conditions

By the catalysis of palladium(0), S-allyl thiocarbamates 1 react with aryl iodides and vinyl bromides to give allyl aryl sulfides and allyl vinyl sulfides, respectively, in good yields.

Stereoselective formation of allylic sulfides via two sequential [3,3]-sigmatropic rearrangements of allylic xanthates and its mechanistic aspects

O-(2-Alkenyl) S-alkyl dithiocarbonates (allylic xanthates) were pyrolyzed to give 2-alkenyl alkyl sulfides (allylic sulfides) via the corresponding allylically isomeric S-(2-alkenyl) S-alkyl dithiocarbonates. The reaction follows the first-order rate law

Palladium-Catalyzed Synthesis of Allylic and Benzylic Sulifides from the Corresponding Dithiocarbonates

Allylic and benzylic sulfides are prepared from O-(2-alkenyl) or S-(2-alkenyl) S-alkyl and O-benzyl S-alkyl dithiocarbonates in the presence of palladium(0)-phosphine complex as a catalyst.

One-Flask Synthesis of Sulfides from Alcohols and Alkyl Halides Using Benzoxazoline-2-thione

The synthesis of sulfides from alcohols and benzoxazoline-2-thione (I) was studied to establish its generality and the mechanism of the reaction.A one-flask synthesis of sulfides from alcohols was developed.According to this procedure, various sulfides were prepared without the use of illsmelling thiols.Moreover, partial sulfenylation of diols to give sulfenyl alcohols was achieved.Keywords - one-flask synthesis; benzoxazoline-2-thione; partial sulfenylation; sulfide; sulfenyl alcohol

A CONVENIENT AND STEREOSELECTIVE SYNTHESIS OF ALLYLIC SULFIDES

The fractional distillation of O-(2-alkenyl or 2-cycloalkenyl) S-alkyl dithiocarbonates (xanthates) affords 2-alkenyl or 2-cycloalkenyl alkyl sulfides.The reaction involves the -sigmatropic rearrangement of the xanthates to produce S-(2-alkenyl or 2-cycloalkenyl) S-alkyl dithiocarbonates followed by extrusion of carbon oxysulfide to give 2-alkenyl or 2-cycloalkenyl alkyl sulfides.

Novel Synthetic Reactions Using Bis(2,2,2-trifluoroethoxy)diorganosulfuranes

Alkoxy- or acyloxysulfuranes prepared in situ by the ligand exchange of bis(2,2,2-trifluoroethoxy)diorganosulfuranes with alcohols or carboxylic acids were found to behave as a potential alkylating or acylating reagent for the preparation of unsymmetrical sulfides, ketones, and esters.