Flavanoids. Part 6. The kinetics and mechanism of base-catalysed isomerisation of 3-arylideneflavanones

Dhavale, Dilip Dattatraya ; Joshi, Poonam ; Marathe, Keshav Gangadhar (1987) Flavanoids. Part 6. The kinetics and mechanism of base-catalysed isomerisation of 3-arylideneflavanones Journal of the Chemical Society, Perkin Transactions 2 (4). pp. 449-452. ISSN 1364-5471

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Official URL: http://pubs.rsc.org/en/content/articlelanding/1987...

Related URL: http://dx.doi.org/10.1039/P29870000449

Abstract

Base-catalysed Z→E conversion of 3-arylideneflavanones provide a unique system suitable for kinetic studies by 1H n.m.r. spectroscopy. Isomerisation studies of 10 enones in [2H5] pyridine showed that a first-order unimolecular reaction was taking place. The Hammett σ-ρ relationship is not adequate to accommodate the substituent effect on rate in the case of p- and m-nitro-3-benzylidene derivatives. The unusual case of the nitro substituent is discussed.

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