title: Comparison of the Relative Reactivities of the Triisopropylsilyl Group With Two Fluorous Analogs.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
authors.forename: Amador Garcia
authors.initials: AG
authors.lastname: Sancho
authors.forename: Xiao
authors.initials: X
authors.lastname: Wang
authors.forename: Bin
authors.initials: B
authors.lastname: Sui
authors.forename: Dennis
authors.initials: D
authors.lastname: Curran