174316-02-0Relevant articles and documents
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.
Synthesis of α-methylene-β-hydroperoxy sulfoxides by regioselective photooxygenation (Schenck Reaction) of racemic vinyl sulfoxides
Adam,Kumar,Saha-Moller
, p. 1525 - 1528 (2007/10/02)
The β-hydroperoxy vinyl sulfoxides 3 were synthesized in good to excellent yields by regioselective photooxygenation of racemic vinyl sulfoxides 2. Moderate diastereoselectivities were observed in the ene reaction of singlet oxygen (Schenck Reaction) with
