13307-56-7Relevant academic research and scientific papers
Catalyst-dependent selective synthesis of O/S- and S/S-acetals from enol ethers
Braga,Silveira,Dornelles,Zeni,Galarza,Wessjohann
, p. 3155 - 3162 (1995)
Enol ethers are reacted with mercaptanes to give the corresponding O/S- or S/S-acetals in medium to high yield. Either product can be formed selectively depending on the acid catalyst and the reaction time applied.
Reaction of Pummerer Rearrangement Intermediates with Sulfides and Thiols. Synthesis of Sulfonium Salts and Dithioacetals
Tanikaga, Rikuhei,Hiraki, Yuji,Ono, Noboru,Kaji, Aritsune
, p. 41 - 42 (1980)
Sulfides (5) and thiols (6) react instantly with the Pummerer rearrangement intermediates (3) at 0 deg C to give sulfonium salts (7) and dithioacetals (8), respectively.
Synthesis of dithioacetals and oxathioacetals with chiral auxiliaries
Zaidi, Javid H.,Naeem, Fazal,Khan, Khalid M.,Iqbal, Rasfaid,Zia-Ullah
, p. 2641 - 2653 (2007/10/03)
One-pot synthesis of dithioacetals as well as an efficient method for oxathioacetal is reported. Additionally, some chiral auxiliaries were used to synthesize enantiomerically pure dithioacetals and oxathioacetals.
Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 15. Generation of alkoxycarbonyl(sulfenyl)carbenes and their intramolecular insertion to give alkenyl sulfides
Aitken, R. Alan,Armstrong, Jill M.,Drysdale, Martin J.,Ross, Fiona C.,Ryan, Bruce M.
, p. 593 - 604 (2007/10/03)
A range of 18 alkoxycarbonyl sulfinyl phosphorus ylides 9 have been prepared and their behaviour upon flash vacuum pyrolysis (FVP) at 600 deg C examined. For R1 = H, Me and Et they lose Ph3PO and in some cases Ph3P to give mixtures of products including the alkenyl sulfides 10, the sulfides 11, the disulfides 12 and the thioesters 14. The alkenyl sulfides 10 most likely arise from intramolecular insertion of the alkoxycarbonyl sulfenyl carbenes resulting from loss off Ph3PO to produce β-lactones which then lose CO2 and this is supported by the results from 13C labelled ylides. Possible mechanisms for the formation of 11 and 14 are also presented and the feasibility of various steps has been examined by preparation and pyrolysis of the proposed intermediates. In contrast, pyrolysis of the ylides 9 where R1 = Ph and the tert-butoxycarbonyl ylides 30 leads mainly to complete fragmentation with loss of Ph3PO and benzyl alcohol or 2-methylpropan-2-ol and does not give any useful sulfur-containing products. Four alkoxy-carbonyl sulfonyl diazo compounds 33 have been prepared and in three cases they give the alkenyl sulfones 34 upon FVP at 400 deg C, probably by an intramolecular insertion and decarboxylation process analogous to the formation of 10 from 9. On the other hand the alkoxycarbonyl carbenes produced by FVP of the amino acid-derived diazo compounds 35 undergo alternative proocesses with no sign of β-lactone formation. Fully assigned 13C NMR data are presented for 13 of the ylides.
Aggregative activation and carbanion chemistry: Complex base deprotonation and directed functionalisation of dithioacetals
Gros, Philippe,Hansen, Philippe,Caubere, Paul
, p. 15147 - 15156 (2007/10/03)
Bis(phenylthio)methane and [1,3]-dithiane were efficiently deprotonated by the NaNH2-Et(OCH2CH2)2-ONa complex base. A marked behaviour difference was observed between the sodium carbanion of [1,3]-dithiane and the corresponding lithio-derivative. A 'radicaloid' mechanism is proposed to explain the results observed.
Reactions of Sulfoxides with Magnesium Amides. Transformations of Sulfoxides into Sulfides, Dithioacetals and Vinyl Sulfides
Kobayashi, Kazuhiro,Kawakita, Masataka,Yokota, Kouichi,Mannami, Tohru,Yamamoto, Koji,et al.
, p. 1401 - 1408 (2007/10/02)
The reactions of sulfoxides with magnesium amides generated in situ from the reaction of ethylmagnesium bromide and seconday amines, such as diisopropylamine (DIPA) or 2,2,6,6-tetramethylpiperidine (TMP) in diethyl ether, were examined.Diaryl sulfoxides were heated with the diisopropylaminomagnesium reagent in diethyl ether to give the corresponding diaryl sulfides in 42-52percent yields.Sulfoxides bearing hydrogens at the α-position only(RSOCH2R1) reacted with the tetramethylpiperidinomagnesium reagent at room temperature to produce the corresponding dithioacetals (RSCHR1SR) in 47-86percent yields.The treatment of sulfoxides bearing hydrogens both at the α-and β-positions (RSOCHR1CHR2R3) with the magnesium amides at room temperature afforded the corresponding vinyl sulfides (RSCR1=CR2R3) in 52-72percent yields accompanying 2.3-27percent yields of the corresponding dithioacetals.The pathways leading to the products involving the formation of the sulfur-stabilized carbonium ion intermediates are discussed.
A General Preparative Method for Carbonyl-Protected γ-Lithioketones via Reductive Lithiation. Synthetic Uses of the Bishomoenolate Equivalents
Cohen, Theodore,Zhang, Birong,Cherkauskas, John P.
, p. 11569 - 11584 (2007/10/02)
The mixed cuprates, generated by reductive lithiation of bis(phenylthio)acetals using lithium 4,4'-di-tert-butylbiphenylide (LDBB), followed by addition of cuprous bromide-dimethyl sulfide complex, undergo conjugate addition to enones in the presence of t
Organic Syntheses without Solvent: Preparation of Sulfones and Dithioacetals
Bram, Georges,Loupy, Andre,Roux-Schmitt, Marie Claude,Sansoulet, Jean,Strzalko, Tekla,Seyden-Penne, Jacqueline
, p. 56 - 59 (2007/10/02)
Sulfones are prepared by alkylation of sulfinate salts under solid-liquid phase-transfer catalysis without solvent; dithioacetals are obtained by heterogeneous uncatalyzed reactions of potassium arenethiolates and gem-dihaloalkanes.In both cases, the yields are high and the reaction conditions are mild.Some limitations are given.
Novel Alumina-catalysed Reactions of Arylthioalkyl Halides and Related Compounds
Jigajinni, Veerappa B.,Wightman, Richard H.
, p. 1801 - 1812 (2007/10/02)
Arylthioalkyl halides of the type ArS(CH2)nCl (Ar = phenyl or substituted phenyl, n = 1-4) undergo rearrangement on heating with neutral alumina to 1,n-bis(arylthio)alkanes of type ArS(CH2)nSAr in high yield.Similar rearrangements occur with some closely related structural types.The bis(arylthio)alkanes undergo further reaction with alumina at higher temperatures in air giving diaryl disulphides.Bis(o-iodophenylthio)methane eliminates iodine on heating with alumina, producing dibenzodithiepin.Some observations concerning the mechanism are presented.
Synthesis of Aldehydes from Phenylthiotrimethylsilylmethane
Ager, David J.
, p. 1131 - 1136 (2007/10/02)
Phenylthiotrimethylsilylmethyl-lithium (4) reacts with alkyl halides to give 1-phenylthio-1-trimethylsilylalkanes (5), which can also be prepared by the addition of alkyl-lithium to 1-phenylthio-1-trimethylsilylethene (8), or from bis(phenylthio)acetals (11).The 1-phenylthio-1-trimethylsilylalkanes (5) can be converted into the corresponding aldehyde (15) by oxidation to the sulphoxide (13), thermal rearrangement, and hydrolysis of the resultant O-silyl thioacetal (14).
