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Issue 41, 2010
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Efficient synthesis of tetradecafluoro-4-phenylheptan-4-ol by a Cannizzaro-type reaction and application of the alcohol as a bulky Martin ligand variant for a new anti-apicophilic phosphorane

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Abstract

Alcohols 8 bearing two identical perfluoroalkyl groups were prepared by the reaction of the corresponding perfluoroalkyl phenyl ketones 7 with 0.5 equivalents of t-BuOK via Cannizzaro-type disproportionation. Utilizing the new bulky bidentate ligand with two n-C3F7 groups generated from 8c, anti-apicophilic phosphorane 5a and its stable isomer 6a were synthesized. The crystal structures of 5a and 6a were slightly affected by the steric repulsion of heptafluoropropyl groups. Kinetic studies on the isomerization of 5a to 6a showed that the new ligand was effective for decreasing the isomerization rate compared with its C2F5 analog 3a to about half.

Graphical abstract: Efficient synthesis of tetradecafluoro-4-phenylheptan-4-ol by a Cannizzaro-type reaction and application of the alcohol as a bulky Martin ligand variant for a new anti-apicophilic phosphorane

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Publication details

The article was received on 25 May 2010, accepted on 06 Aug 2010 and first published on 22 Sep 2010


Article type: Paper
DOI: 10.1039/C0DT00539H
Dalton Trans., 2010,39, 9823-9829

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    Efficient synthesis of tetradecafluoro-4-phenylheptan-4-ol by a Cannizzaro-type reaction and application of the alcohol as a bulky Martin ligand variant for a new anti-apicophilic phosphorane

    X. Jiang, S. Matsukawa, K. Kakuda, Y. Fukuzaki, W. Zhao, L. Li, H. Shen, S. Kojima and Y. Yamamoto, Dalton Trans., 2010, 39, 9823
    DOI: 10.1039/C0DT00539H

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