5746-94-1Relevant articles and documents
Br?nsted acid-mediated ring-opening reactions of methylenecyclopropanes: A dramatic counter ion effect
Shao, Li-Xiong,Huang, Jin-Wen,Shi, Min
, p. 11895 - 11901 (2004)
We report herein two different ring-opening patterns of methylenecyclopropanes (MCPs) in the presence of two Br?nsted acids heptadecafluorooctane-1-sulfonic acid (C8F17SO 3H) and toluene p-sulfonic acid (TsOH) under mild conditions: (a) the ring-opening of MCPs by H2O and subsequent etherification give the corresponding homoallylic ethers in the presence of heptadecafluorooctane-1- sulfonic acid; (b) the direct ring-opening of MCPs by the Br?nsted acid gives the corresponding homoallylic alcohol derivatives in the presence of toluene p-sulfonic acid. We report two different ring-opening patterns of methylenecyclopropanes (MCPs) in the presence of two Br?nsted acids heptadecafluorooctane-1-sulfonic acid (C8F17SO 3H) and toluene p-sulfonic acid (TsOH): (a) the ring-opening of MCPs by H2O and subsequent etherification give the corresponding homoallylic ethers in the presence of heptadecafluorooctane-1-sulfonic acid; (b) the direct ring-opening of MCPs by the Br?nsted acid gives the corresponding homoallylic alcohol derivatives in the presence of toluene p-sulfonic acid.