Regioselective radical cyclization initiated by the reaction of allylic hydroperoxides with iron(II) sulfate
作者:Araki Masuyama、Tomohiro Sugawara、Masatomo Nojima、Kevin J McCullough
DOI:10.1016/s0040-4020(02)01522-3
日期:2003.1
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
与硫酸亚铁的混合物1-甲基-2-亚甲基-1-环己基氢过氧化物的治疗4 /的CuCl 2,得到1-(1-氯环)乙酮,与6-一致主要产物内切- trig的中间体5- acetylhex的环化-5-烯基。该策略扩展到一系列1-异丙烯基环烷基氢过氧化物的扩环。区域选择性7-或8-内切- trig的环化反应可通过处理相应的环戊基或环己基氢过氧化物的用任一个的FeSO的混合物来实现4 /的CuCl 2或的FeSO 4只。取代基对8-效率的影响远藤- trig的环化过程中还探讨。