Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene
作者:Matthew S. McVeigh、Andrew V. Kelleghan、Michael M. Yamano、Rachel R. Knapp、Neil K. Garg
DOI:10.1021/acs.orglett.0c01510
日期:2020.6.5
development of alternative precursors. We report the syntheses of silyl tosylate precursors to cyclohexyne, 1,2-cyclohexadiene, and 1,2-cycloheptadiene. The resultant strained intermediates undergo trapping in situ to give cycloaddition products. Additionally, the results of competition experiments between silyl triflates and silyl tosylates are reported.
瞬态应变环状中间体已成为现代合成化学中有价值的中间体。尽管三氟甲硅烷基甲硅烷基酯前体最常用于过滤中间体,但某些甲硅烷基三氟甲磺酸酯的不稳定性保证了替代前体的发展。我们报告了甲硅烷基甲苯磺酸盐前体的合成环己炔,1,2-环己二烯和1,2-环庚二烯。所得的应变中间体原位捕集,得到环加成产物。另外,报告了甲硅烷基三氟甲磺酸酯和甲苯磺酸甲硅烷基酯之间的竞争实验结果。