Catalytic use of organostannyl radical: The reaction of 1,2,3-selenadiazole with olefins in the presence of a catalytic amount of tributyltin hydride
β Scribed by Yutaka Nishiyama; Yasunobu Hada; Masahiro Anjiki; Sakiko Hanita; Noboru Sonoda
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 223 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
When 1,2,3-selenadiazoles were treated with an excess amount of olefins in the presence of a catalytic amount of Bu3SnH and AIBN, the addition of a vinyl radical, which was generated in situ by the denitrogenation of 1,2,3-selenadiazoles, to the carbon-carbon double bond followed by intramolecular cyelization proceeded efficiently to afford the corresponding dihydroselenophenes in moderate to good yields.
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An interesting 2,4-syn dialkyl diastereoselection has been observed in the radical debromination of a-bromo-a-methyld-valerolactones. The reaction of 4-alkyl-2-bromo-3-hydroxy-2-methyl-5-pentanolides with Bu 3 SnH and a catalytic amount of Et 3 B gave, essentially, a single diastereomer with a 2,4-s