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Scope and Limitation of the Reactions of 3-Imino Derivatives of Pentane-2,4-Diones with Organophosphorus Reagents
Authors:Leila S Boulos  Hoda A Abdel-Malek  Naglaa F El-Sayed  Maysa E Moharam
Institution:1. Department of Organometallic and Organometalloid Chemistry , NRC , Dokki , Cairo , Egypt;2. Department of Microbial Chemistry , NRC , Dokki , Cairo , Egypt
Abstract:Abstract

3-(Hydroxyimino)pentane-2,4-dione reacts with phosphonium ylides, Wittig–Horner reagents, trialkyl phosphites, and Lawesson's reagents to give the olefinic and cyclic products, the phosphonate adducts, the dialkyl phosphate products, the phosphinodithioic acid, and 2,4-dithione products, respectively. Furthermore, the reaction of 3-(phenylimino)pentane-2,4-dione with Wittig, Wittig–Horner reagents and trialkyl phosphite resulted in the formation of 2,5-diendioate, diethoxy phosphoryl hexanoate and the phosphate products. Possible reaction mechanisms are considered and the structural assignments are based on analytical and spectroscopic results. The antibacterial and antifungal activities for some of the new compounds are also reported.
Keywords:3-Substituted pentane-2  4-diones  alkyl phosphites  ylides  Wittig–Horner reagents  Lawesson’s reagent
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