ISSN:
1042-7163
Keywords:
Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Diphenylphosphine oxide (1′) reacts reversibly with a 10-methylacridinium salt (2) in acetonitrile at 20°C to equilibrate with a new salt 3 formed by the addition of 1′ to the cation of 2. The forward reaction in this equilibrium proceeds via nucleophilic attack by the phosphorus atom of diphenylphosphinous acid (1), the trivalent tautomer of 1′, upon the 9-carbon atom of the cation of 2, forming a phosphorus-carbon covalent bond. The equilibrium constant has been determined by UV-vis and 1H NMR spectroscopy as well as by HPLC analysis. The reaction has been analyzed kinetically, and the results have been compared with those obtained in the similar reaction of an alkyl ester of 1, the diphenylphosphinite (5), with 2 that gives the phosphonium salt 6. It is suggested that 6 is much more stable than 3.The equilibrium constant for the tautomerism between 1′ and 1 has also been estimated. © 1995 John Wiley & Sons, Inc.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hc.520060513
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