Sancho Amador Garcia, Wang Xiao, Sui Bin, Curran Dennis
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
Adv Synth Catal. 2009 May 1;351(7-8):1035-1040. doi: 10.1002/adsc.200900061.
The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silyl and diisopropyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadeca-fluoroundecyl)silyl [C(8)F(17)(CH(2))(n)Si(i-Pr)(2), where n = 2 or 3], of the standard triisopropylsilyl (TIPS) group are compared in the setting of alcohol protection. The fluorous silyl groups can be installed under standard conditions in comparable yields to the TIPS group, but the derived fluorous silyl ethers are more labile than TIPS ethers towards cleavage by both acids and fluoride.
在醇保护的背景下，比较了标准三异丙基甲硅烷基（TIPS）基团的两种氟代类似物，二异丙基（3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10 - 十七氟癸基）甲硅烷基和二异丙基 - （4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11 - 十七氟十一烷基）甲硅烷基[C(8)F(17)(CH(2))(n)Si(i-Pr)(2)，其中n = 2或3]的相对稳定性。氟代甲硅烷基团可以在标准条件下以与TIPS基团相当的产率引入，但衍生的氟代甲硅烷基醚在酸和氟化物的作用下比TIPS醚更不稳定，更容易发生裂解。
