114597-58-9Relevant academic research and scientific papers
A comparison of hydrogen bonding solvent effects on the singlet oxygen reactions of allyl and vinyl sulfides, sulfoxides, and sulfones
Stensaas, Kristina L.,McCarty, Brent V.,Touchette, Natacha M.,Brock, James B.
, p. 10683 - 10687 (2006)
The singlet oxygen (1Δg) photooxidations of 2-methyl-3-phenylthio-2-butene (1a), 1-[(4-nitrophenyl)thio]-2,3-dimethyl-2-butene (2c), 2-methyl-3-phenylsulfinyl-2-butene (3), 2-methyl-3-phenylsulfonyl-2-butene (6), and 1-[(4-nitrophenyl)sulfonyl]-2,3-dimethyl-2-butene (7c) were conducted in the following deuterated solvents: acetonitrile, benzene, chloroform, methanol, or methanol/water mixture. In each case the ene allylic hydroperoxide products and/or the [2+2] cycloaddition products were quantified and inspected for possible hydrogen bonding induced differences in product selectivity and regiochemistry. After comparison to literature values for related substrates, the results indicate that only photooxidations of vinyl sulfides are susceptible to hydrogen bonding solvent effects.
Pathways and Stereochemistry of Rearrangements in Reactions of Sulfenyl Chlorides with Alkenes
Borisov, A. V.,Bodrikov, I. V.,Borisova, G. N.,Smit, V. A.,Lutsenko, A. I.,Bel'skii, V. K.
, p. 943 - 951 (2007/10/03)
In reactions of 3,3-dimethyl-1-butene and 3-methyl-1-butene with 2,4-dinitrobenzenesulfenyl chloride in the systems M(ClO4)n-CH3NO2 (M=Li or Mg), 1,2 shifts of the methyl group and hydride ion respectively occur directly within the AdE process (? pathway of the rearrangement).In the same systems reactions of these alkenes with arenesulfenyl chlorides containing in the electrophilic moiety less electronegative substituents, as compared to the dinitrophenyl group, initially yield β-chloro sulfides, which under reaction conditions mostly undergo rearrangements (? pathway of the rearrangement).In nitromethane in the presence of LiClO4, AlCl3, or AgBF4 erythro-2-arylthio-1-chloro-1-deutero-2,3-dimethylbutanes are converted into stereoisomeric thiochromans; their ratio is controlled by the nature of the metal compound added, electronic properties of substituents in the arylthio moiety, and reaction temperature.
Temperature, Solvent, and Substituent Effects on the Singlet Oxidations of Allylic Phenyl Sulfoxides, Sulfones, and Sulfides
Clennan, Edward L.,Chen, Xiangning
, p. 8212 - 8218 (2007/10/02)
The reaction of singlet oxygen with a series of allylic sulfoxides, sulfones, and sulfides have been examined as a function of extent of reaction, temperature, and solvent.Hydroperoxy groups but not alkyl, hydrogen, or hydroxyl on chiral carbons β to sulfide sulfur induce diastereoselective sulfoxide formations.Evidence is presented that suggests that the oxidation at sulfur occurs with anchimeric assistance from the hydroperoxy group via a favorable sulfurane-like transition state.
