Lewis acid base chemistry of Bestmann's ylide, Ph3PCCO, and its bulkier analogue, (cyclohexyl)3PCCO

Amandeep Brar; Daniel K. Unruh; Adelia J. Aquino; Clemens Krempner

doi:10.1039/C9CC01239G

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Lewis acid base chemistry of Bestmann's ylide, Ph₃PCCO, and its bulkier analogue, (cyclohexyl)₃PCCO†

Amandeep Brar,^a Daniel K. Unruh,

^a Adelia J. Aquino

^b and Clemens Krempner*^a

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* Corresponding authors

^a Department of Chemistry and Biochemistry, Texas Tech University, Memorial Dr & Boston, Lubbock, TX, USA
E-mail: clemens.krempner@ttu.edu
Fax: +1-806-742-1289
Tel: +1-806-834-3507

^b School of Pharmaceutical Science and Technology, Tianjin University, 300072 Tianjin, People's Republic of China

Abstract

The new phosphoranylideneketene, (cyclohexyl)₃PCCO, was synthesized and structurally as well as spectroscopically characterized. Ph₃PCCO and (cyclohexyl)₃PCCO were found to be weak ambidentate Lewis bases capable of donating to strong Lewis acids via the ylidic carbon or the carbonyl oxygen.

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Article information

DOI: https://doi.org/10.1039/C9CC01239G
Article type: Communication
Submitted: 12 Feb 2019
Accepted: 26 Feb 2019
First published: 04 Mar 2019

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Chem. Commun., 2019,55, 3513-3516

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Lewis acid base chemistry of Bestmann's ylide, Ph₃PCCO, and its bulkier analogue, (cyclohexyl)₃PCCO

A. Brar, D. K. Unruh, A. J. Aquino and C. Krempner, Chem. Commun., 2019, 55, 3513 DOI: 10.1039/C9CC01239G

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