کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5226090 | 1383566 | 2006 | 5 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: A comparison of hydrogen bonding solvent effects on the singlet oxygen reactions of allyl and vinyl sulfides, sulfoxides, and sulfones A comparison of hydrogen bonding solvent effects on the singlet oxygen reactions of allyl and vinyl sulfides, sulfoxides, and sulfones](/preview/png/5226090.png)
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.
The 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.
Journal: Tetrahedron - Volume 62, Issue 46, 13 November 2006, Pages 10683-10687