Reaction of 2-thioxo-4-thiazolidinones toward Lawesson's reagent, phosphorus pentasulfide, dialkylaminophosphines, and phosphorus ylides

摘要

2-Thioxo3-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. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the related elements to view the free supplemental file.