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Comparison of the relative reactivities of the triisopropylsilyl group with two fluorous analogs

Sancho, AG and Wang, X and Sui, B and Curran, DP (2009) Comparison of the relative reactivities of the triisopropylsilyl group with two fluorous analogs. Advanced Synthesis and Catalysis, 351 (7-8). 1035 - 1040. ISSN 1615-4150

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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 [C8F 17(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. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Sancho, AG
Wang, X
Sui, B
Curran, DPcurran@pitt.eduCURRAN
Date: 1 May 2009
Date Type: Publication
Journal or Publication Title: Advanced Synthesis and Catalysis
Volume: 351
Number: 7-8
Page Range: 1035 - 1040
DOI or Unique Handle: 10.1002/adsc.200900061
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1615-4150
PubMed Central ID: PMC2772155
PubMed ID: 20160880
Date Deposited: 21 Feb 2013 22:51
Last Modified: 05 Mar 2019 16:55
URI: http://d-scholarship.pitt.edu/id/eprint/17362

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