1798-84-1Relevant articles and documents
Indium-mediated, highly efficient cyclopropanation of olefins using CH 2I2 as methylene transfer reagent
Virender,Jain, Suman L.,Sain, Bir
, p. 37 - 38 (2005)
The indium-mediated, one-pot cyclopropanation of a variety of olefins with methylene iodide proceeds smoothly with excellent yields of products.
Silylium-Ion-Promoted Ring-Opening Hydrosilylation and Disilylation of Unactivated Cyclopropanes
Bonetti, Vittorio,Klare, Hendrik F. T.,Oestreich, Martin,Roy, Avijit,Wang, Guoqiang,Wu, Qian
supporting information, (2020/02/04)
A silylium-ion-promoted ring-opening hydrosilylation of unactivated cyclopropanes is reported. The reaction is facilitated by the γ-silicon effect, and the regioselectivity is influenced by various stabilizing effects on the carbenium-ion intermediates, including the β-silicon effect. The experimental observations are in accord with the computed reaction mechanism. The work also showcases the ability of silylium ions to isomerize cyclopropyl to allyl groups, and the resulting α-olefins engage in a silylium-ion-mediated disilylation with hexamethyldisilane.
Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes
Wang, Di,Xue, Xiao-Song,Houk, Kendall N.,Shi, Zhuangzhi
supporting information, p. 16861 - 16865 (2018/11/27)
The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.