Reaction of 2-Thioxo-4-Thiazolidinones Toward Lawesson's Reagent, Phosphorus Pentasulfide, Dialkylaminophosphines, and Phosphorus Ylides

HA Abdel-Malek - Phosphorus, Sulfur, and Silicon and the Related …, 2012 - Taylor & Francis
Phosphorus, Sulfur, and Silicon and the Related Elements, 2012Taylor & Francis
Thioxo—3-allyl-4-thiazolidinone 1a reacts with Lawesson's reagent (LR, 2) to give the
ethylenic product 5 through a coupling reaction along with the dithioxo compound 6.
Coupling reaction products of types 8 and 9 are also produced upon reacting
thiazolidinones 1 and with the appropriate tris (diallkylamino) phosphine reagent (3 a, b).
Reaction of the thiazolidinone 1a with the ylidenetriphenylphosphorane reagents 4 a–c
proceeds according to the Wittig mechanism yielding ethylenes 10a–c, respectively …
Abstract
2-Thioxo—3-allyl-4-thiazolidinone 1a reacts with Lawesson's reagent (LR, 2) to give the ethylenic product 5 through a coupling reaction along with the dithioxo compound 6. Coupling reaction products of types 8 and 9 are also produced upon reacting thiazolidinones 1 and with the appropriate tris(diallkylamino) phosphine reagent (3 a,b). Reaction of the thiazolidinone 1a with the ylidenetriphenylphosphorane reagents 4 a–c proceeds according to the Wittig mechanism yielding ethylenes 10a–c, respectively. Structural elucidations for the new products were based upon compatible analytical and spectroscopic measurements as well a confirmatory single crystal X-ray structure for 5.
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