Curran, DP and Wang, X and Zhang, Q
(2005)
Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines.
Journal of Organic Chemistry, 70 (9).
3716 - 3719.
ISSN 0022-3263
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Abstract
(Equation Presented) The relative reactivities of triphenylphosphine (PPh3) and three fluorous triarylphosphines [(p-RF(CH 2)2C6H4)nPPh 3-n, where n = 1-3] have been compared in internal competition experiments. Product ratios were determined by 31P NMR spectroscopy. The four phosphines have about the same reactivities in oxidation, alkylation, and Staudinger reactions and give comparable yields in a preparative Mitsunobu reaction. Previously observed rate and yield differences in Staudinger reactions of the fluorous phosphines are attributed to solubility effects, not reactivity differences. A light fluorous phosphine [(p-C8F17(CH 2)2C6H4PPh2] outperforms a commercially available resin-bound phosphine in a competitive benzylation experiment by a factor of about 4. © 2005 American Chemical Society.
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Details
Item Type: |
Article
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Curran, DP | curran@pitt.edu | CURRAN | | Wang, X | | | | Zhang, Q | | | |
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Date: |
29 April 2005 |
Date Type: |
Publication |
Journal or Publication Title: |
Journal of Organic Chemistry |
Volume: |
70 |
Number: |
9 |
Page Range: |
3716 - 3719 |
DOI or Unique Handle: |
10.1021/jo050116j |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
0022-3263 |
MeSH Headings: |
Catalysis; Hydrocarbons, Fluorinated--chemistry; Indicators and Reagents; Magnetic Resonance Spectroscopy; Molecular Structure; Phosphines--chemistry |
PubMed ID: |
15845013 |
Date Deposited: |
23 Jul 2013 15:55 |
Last Modified: |
25 Jun 2021 01:55 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/19394 |
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