| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5226090 | Tetrahedron | 2006 | 5 Pages |
The singlet oxygen (1Îg) 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.
Graphical abstractDownload full-size imageThe singlet oxygen photooxidation of several allyl and vinyl sulfides, sulfoxides, and sulfones were conducted in deuterated solvents. The results indicate that only vinyl sulfides are suspectible to hydrogen bonding solvent effects.
