Title of article :
Regioselective radical cyclization initiated by the reaction of allylic hydroperoxides with iron(II) sulfate
Author/Authors :
Araki Masuyama، نويسنده , , Tomohiro Sugawara، نويسنده , , Masatomo Nojima، نويسنده , , Kevin J McCullough، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2003
Pages :
14
From page :
353
To page :
366
Abstract :
Treatment of 1-methyl-2-methylene-1-cyclohexyl hydroperoxide with a mixture of FeSO4/CuCl2 yielded 1-(1-chlorocyclohexyl)ethanone as the major product consistent with 6-endo-trig cyclization of the intermediate 5-acetylhex-5-enyl radical. This strategy was extended to the ring enlargement of a series of 1-isopropenylcycloalkyl hydroperoxides. Regioselective 7- or 8-endo-trig cyclization reactions could be achieved by treatment of the corresponding cyclopentyl or cyclohexyl hydroperoxides with either a mixture of FeSO4/CuCl2 or with FeSO4 only. The influence of substituents on the efficiency of the 8-endo-trig cyclization process was also explored.
Keywords :
iron(II) sulfate , endo-trig radical cyclization , allylic hydroperoxide , ring enlargement
Journal title :
Tetrahedron
Serial Year :
2003
Journal title :
Tetrahedron
Record number :
1083809
Link To Document :
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