Markovnikov hydration of vinylcyclopropanes by oxymercuration-demercuration.
作者:Shinya Nishida、Takashi Fujioka、Nobujiro Shimizu
DOI:10.1016/s0022-328x(00)84861-5
日期:1978.8
Representative vinylcyclopropanes (IaIc) were hydrated in a Markovnikov fashion by oxymercuration-demercuration. Isolated yields of α-cyclopropyl-substituted alcohols were more than 80%. 2,2-Diphenyl-l-vinylcyclopropane (Id) was the only olefin that produced a mixture of the expected alcohol, IId, and a rearranged product III. At 0° C, However, the amount of III was minimal (ca. 6%), and hence the
代表性的乙烯基环丙烷(IaIc)以马尔可夫尼可夫的方式通过氧化汞-脱汞水合。α-环丙基取代的醇的分离产率超过80%。2,2-二苯基-1-乙烯基环丙烷(Id)是唯一产生预期醇IId和重排产物III的混合物的烯烃。然而,在0°C下,III的量极少(约6%),因此实现了Id的马尔可夫尼科夫水合。通过用硼氢化氘化钠脱汞证明了在III的生成过程中消耗了2摩尔当量的乙酸汞。