Comparison of the Relative Reactivities of the Triisopropylsilyl Group With Two Fluorous Analogs

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‐heptadecafluoroundecyl)silyl [C8F17(CH2)nSi(i‐Pr)2, where n=2 or 3], of the standard triisopropylsilyl (TIPS) group...

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Bibliographic Details
Published in:	Advanced synthesis & catalysis Vol. 351; no. 7‐8; pp. 1035 - 1040
Main Authors:	Sancho, Amador Garcia, Wang, Xiao, Sui, Bin, Curran, Dennis P.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY‐VCH Verlag 01-05-2009
Subjects:	fluorous chemistry protecting groups relative reactivity triisopropylsilyl group
Online Access:	Get full text
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Summary:	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‐heptadecafluoroundecyl)silyl [C8F17(CH2)nSi(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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1
ISSN:	1615-4150 1615-4169
DOI:	10.1002/adsc.200900061