17872-92-3

Usage

Purification Methods

Fractionate it at high vacuum and recrystallise it from pentane at -80o. If too impure (cf IR), dissolve it in CH2Cl2 (ca 800mL for 100g), wash this with 2M aqueous NaOH (2 x 200mL), brine, dry, evaporate and distil it. [Craig et al. J Chem Soc, Perkin Trans 1 1949 1985, IR and NMR: Cooper J Am Chem Soc 76 3713 1954.]

InChI:InChI=1/C10H16O2SSi/c1-14(2,3)9-13(11,12)10-7-5-4-6-8-10/h4-8H,9H2,1-3H3

Upstream product

• 17873-08-4 (phenylsulfanylmethyl)trimethylsilane 
• 18789-72-5 Phenyl trimethylsilylmethyl sulfoxide 
• 75-77-4 chloro-trimethyl-silane 
• 3112-85-4 methylphenylsulfonate 
• 100-68-5 methyl-phenyl-thioether 
• 930-69-8 sodium thiophenolate 

Downstream Products

• 82751-28-8 1-((E)-2-Benzenesulfonyl-vinyl)-piperidine 
• 91787-37-0 1-phenylsulphonyl-1-trimethylsilylpropane 
• 5535-48-8 PVS 
• 26189-62-8 phenyl 2,2-diphenylethenyl sulfone 
• 91787-36-9 1-phenylsulphonyl-1-trimethylsilylpentane 
• 100289-46-1 cycloprop-1-enyl phenyl sulphone 
• 16212-06-9 phenyl styryl sulfone 
• 100289-55-2 1-acetoxy-1-phenyl-2-trimethylsilylethyl phenyl sulphone 
• 5418-11-1 phenyl styryl sulfone 
• 28975-80-6 Phenyl-propenyl-sulfon 
• 91787-24-5 1-phenylsulphonylhept-1-ene 
• 74858-07-4 (E)-1-dimethylamino-2-phenylsulfonylethylene 
• 97399-03-6 benzenesulfonylmethane 
• 935656-86-3 Dilithio(phenylsulfonyl)trimethylsilylmethan 

Relevant academic research and scientific papers

Azetidine derivatives, their preparation and pharmaceutical compositions containing them

Compounds of formula: in which R represents a CR1R2, C═C(R5)SO2R6 or C═C(R7)SO2alk radical, their preparation and the pharmaceutical compositions containing them.

Mild and Selective Oxygenation of Sulfides to Sulfoxides and Sulfones by Perfluoro-cis-2,3-dialkyloxaziridines

Sulfides are oxidized to sulfoxides by stoichiometric amounts of perfluoro-cis-2,3-dialkyloxaziridines 2.The reactions proceed at -40 deg C with nearly complete selectivity and very good yields.Sulfoxides are also oxidized easily by 2 under mild conditions to corresponding sulfones.The oxidation of some bioactive sulfides (promazine, albendazole, biotin, and others) is also reported.

Reagents for rapid peptide synthesis

This invention relates to compounds of the formula: STR1 wherein R is an electron withdrawing group; R1 is H or COZ; X1 and X2 are independently H, lower alkyl, aryl, aryl lower-alkyl or polystyrene or R and X1 taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; and Z is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.

The Synthesis of Ketones via α-Silyl Sulphides

α-Phenylthiosilanes (2) have been prepared by alkylation of the anion (4) derived from the 1-phenylthio-1-trimethylsilylalkane (1).These anions (4) have benn prepared by a variety of methods including, direct deprotonation of (1), displacement of a phenylthio group by lithium naphthalenide addition of an alkyl-lithium to 1-phenylthio-1-trimethylsilylethene (7), and transmetallation of a tributylstannyl moiety.The formation of an alkyl-lithium by reaction of lithium naphthalenide with a phenyl sulphide provided an additional route to (2) from bis(phenylthio)acetals (8).An alternative path to the α-phenylthiosilanes (2) was to reduce the corresponding α-phenylsulphonylsilane (15); these, in turn, being readily available from alkylation or silylation of α-sulphonyl anions.The α-phenylthiosilanes (2) were converted into the O-trimethylsilylphenylthioacetal (18) by the sila-Pummerer rearrangement, although this was complicated by vinyl sulphide (20) formation in certain cases.Subsequent hydrolysis of (18) and (20) gave the ketone (3).

Preparation of Vinylic Sulphones by Peterson Olefination using Phenyl Trimethylsilylmethyl Sulphone

The anion generated from phenyl trimethylsilylmethyl sulphone using butyl-lithium in dimethoxyethane, readily reacts at -78 deg C with various carbonyl compounds to afford vinylic sulphones on work-up at room temperature.The reaction conditions are tolera

Sulfone reagents in organic synthesis. VI. Sulfonyl- and silyl-substituted hydrocarbons as versatile carbanion precursors in organic synthesis

The basic organometallic chemistry of β-silyl-substituted acetylenic, vinylic and alkyl sulfones has been investigated, with attention being given to metallation, carbometallation and the chemical reduction of carbon-carbon unsaturation. 2-Trimethylsilylvinyl and 2-trimethylsilylalkyl sulfones underwent smooth and stereoselective lithiation with RLi on the carbon α to the sulfonyl group. Carbometallation of vinyl sulfones could be achieved with RMgX or LiCuR2, but acetylenic sulfones carbometallated smoothly only with LiCuR2; with RMgX or RLi, these acetylenes underwent alkyldesulfonylation. The utility in synthesis of these metallo derivatives of sulfonyl-silyl-hydrocarbons is discussed and their value in elaborating carbon skeletons is illustrated for the preparation of alkenes, allenes, carbocycles and stereo-defined vinyl sulfones.