Abstract
The singlet oxygen ( 1Δ g) 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.
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