114597-59-0Relevant 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 (2007/10/03)
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.
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.
