1726-02-9Relevant academic research and scientific papers
Imidazole Promoted Highly Efficient Large-Scale Thiol-Free Synthesis of Symmetrical Disulfides in Aqueous Media
Mokhtari, Babak,Kiasat, Ali Reza,Monjezi, Javid
, p. 1573 - 1579 (2015/09/15)
A highly efficient and environmentally friendly method for the imidazole promoted preparation of symmetrical organic disulfides from Bunte salts is described. This thiol-free procedure produces the desired disulfides even on a large scale by reaction of Bunte salts with imidazole in good to high yields in aqueous media.
AN IMPROVED PROCESS FOR THE PREPARATION OF ARMODAFINIL
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Page/Page column 25-26, (2008/06/13)
The invention encompasses processes for preparing intermediates, such as R-modafinic acid or (R)-C1-2 alkyl ester, of modafinic acid, and the conversion of the intermediates to armodafinil.
A convenient synthesis of some symmetrical and unsymmetrical diarylmethyl sulfur and selenium compounds: X-ray crystal structure of diphenylmethylseleno-2-propene and bis[p-chlorophenyl(phenyl)methyl] diselenide
Bhasin,Singh, Neelam,Kumar, Rajeev,Gupta Deepali,Mehta,Klapoetke, Thomas M.,Crawford
, p. 3327 - 3334 (2007/10/03)
A number of novel and synthetically important symmetrical and unsymmetrical diarylmethyl sulfur and selenium compounds have been synthesized and characterized with the help of elemental analysis and various spectroscopic techniques. The methodology employ
Studies on reactions of thioketones with trimethyl(trifluoromethyl)silane catalyzed by fluoride ions
Mloston, Grzegorz,Prakash, G. K. Surya,Olah, George A.,Heimgartner, Heinz
, p. 1644 - 1658 (2007/10/03)
Treatment of 2,2,4,4-tetramethylcyclobutane-1,3-dione (6) in THF with CF3SiMe3 in the presence of tetrabutylammonium fluoride (TBAF) yielded the corresponding 3-(trifluoromethyl)-3-[(trimethylsilyl)oxy]cyclobutanone 7 (Scheme 1) via nucleophilic addition of a CF3- anion at the C=O group and subsequent silylation of the alcoholate. Under similar conditions, the 'monothione' 1 reacted to give thietane derivative 8 (Scheme 2), whereas in the case of 'dithione' 2 only the dispirodithietane 9, the dimer of 2, was formed (Scheme 3). A conceivable mechanism for the formation of 8 is the ring opening of the primarily formed CF3 adduct A followed by ring closure via the S-atom (Scheme 2). In the case of thiobenzophenones 4, complex mixtures of products were obtained including diarylmethyl trifluoromethyl sulfide 10 and 1,1-diaryl-2,2-difluoroethene 11 (Scheme 4). Obviously, competing thiophilic and carbophilic addition of the CF3- anion took place. The reaction with 9H-fluorene-9-thione (5) yielded only 9,9′-bifluorenylidene (14; Scheme 6); this product was also formed when 5 was treated with TBAF alone. Treatment of 4a with TBAF in THF gave dibenzhydryl disulfide (15; Scheme 7), whereas, under similar conditions, 1 yielded the 3-oxopentanedithioate 17 (Scheme 9). The reaction of dithione 2 with TBAF led to the isomeric dithiolactone 16 (Scheme 8), and 3 was transformed into 1,2,4-trithiolane 18 (Scheme 10).
PHASE TRANSFER CATALYZED DESULFURIZATION REACTIONS
Alper, Howard,Sibtain, Fazle,Heveling, Josef
, p. 5329 - 5332 (2007/10/02)
Mercaptans react with triiron dodecarbonyl or dicobalt octacarbonyl, under phase transfer catalysis conditions, to give hydrocarbons in good yields.
Reduction by a Model of NAD(P)H. 36. First and Direct Evidence for the Multi-step Mechanism
Yasui, Shinro,Nakamura, Kaoru,Ohno, Atsuyoshi,Oka, Shinzaburo
, p. 196 - 199 (2007/10/02)
Reductions of thiobenzophenone derivatives with a model compound of NAD(P)H, 1-benzyl-1,4-dihydronicotinamide (BNAH) or N-(α-methylbenzyl)-1-propyl-2,4-dimethyl-1,4-dihydronicotinamide (Me2PNPH), in a solvent containing an O-deuterated alcohol afforded pr
Studies on the Reaction of 3,3,4,4-Tetraphenylthietan-2-one
Charumilind, P.,Kohn, Harold
, p. 4359 - 4365 (2007/10/02)
The chemical reactivity of 3,3,4,4-tetraphenylthietan-2-one (3,3,4,4-tetraphenyl-β-thiolactone, 5) toward nucleophilic, reducing, and oxidizing reagents has been investigated.Compound 5 is relatively inert toward nucleophiles (1-butanethiol, sodium hydroxide, sodium methoxide).The only product obtained from these reactions which cannot be readily attributed to initial thermal fragmentation of the ring is tetraphenylethylene (10).Treatment of 5 with the strong reducing reagent LiAlH4 gave four products upon workup: 2,2,3,3-tetraphenyl-1-propanol (19), 2,2,3,3-tetraphenylpropyl acetate (20), 1,1,3,3-tetraphenyl-2-propanone (7), and 1,1,3-triphenyl-2-indanone (21).The substituted acetone 7 was also obtained when DIBAL was added to 5.Desulfurization experiments with Raney nickel and cobalt catalysts consistently gave 10 in varying amounts.In addition to the alkene 10, compounds 7, 21, and 2,2,3-triphenyl-4,5,6,7-tetrahydro-1-indanone (26) were also isolated with W-2 Raney nickel.Finally, oxidation of 5 with m-chloroperbenzoic acid gave the novel mixed carboxylic-sulfinic acid anhydride (32).This molecule is of particular interest in light of the previous difficulty encountered in the preparation of this class of compounds.Many of the products obtained in these reactions are not those expected based upon previous studies of β-thiolactones.Potential pathways for the origin of the compounds obtained are suggested.
