The behavior of 2-thioxo-4-thiazolidinones toward organophosphorus reagents

The reaction of 2-thioxo-4-thiazolidinone (1a) with phosphorus ylides 2a an d 2b afforded compounds 5 and 6. On the other hand, formylmethyl-enetriphen ylphosphorane (2c) reacts with la and its N-methyl derivative Ib to give th e new complicated phosphoniurn ylides 7a,b, respectively. Reactions of Ib w ith ylides 2a and 2d gave rise to the olefinic compound 8 and the Mew phosp horane product 9. Moreover, dialkyl phosphites 3a,b and trialkyl phosphites 4 a-e react with la to give both the alkylated products 10a-c and the dime ric compounds 11,12. A mechanism is proposed to explain the formation of th e new products. (C) 1999 John Wiley & Sons, Inc.