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Communication | Regular issue | Vol 24, No. 5, 1986, pp.1237-1242
Published online, 1st January, 1970
DOI: 10.3987/R-1986-05-1237
1,3-Anionic Cycloaddition of 1,3-Diphenyl-2-azaallyl Lithium to Thioketenes and Thioketene S-Oxides

Ernst Schaumann,* Helmut Behr, and Gunadi Adiwidjaja

*Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20416 Hamburg, Germany


Cycloaddition of 1,3-diphenyl-2-azaallyl lithium (4) to the thioketenes 5a,b leads to thiazolidines 7a,b. Evidence for an open-chain anionic intermediate 8 is obtained by trapping with methyl iodide and through the stereochemistry of 7a as revealed in an X-ray crystallographic study. With thioketene S-oxides 10a,b, 4 yields thiazoles 15 via a ‘second-generation’ Pummerer reaction.