Newer Methods of Preparative Organic Chemistry by Wilhelm Foerst (Eds.)

By Wilhelm Foerst (Eds.)

More moderen tools of Preparative natural Chemistry V3

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7 0 , 372 (1958). (64d) Leuna-Werke, H. Schade and M . Thiel, German Patent 1063602 (1957). (64e) Leuna-Werke, F. Asinger, M . Thiel, and H . Hauthal, German Patent 1068171 (1957). (65) O. Rohm, German Patent 262707 (1912). (66) H. Reinhardt and J. Szurrat, Gummi u. Asbest 1 0 ( 8 ) , 422-466 (1957). (67) L. Haitinger, Monatsh. Chem. 4 , 165 (1883); S. Onufrowicz, Ber. deut. chem Ges. 2 3 , 3355 (1890); M . Lange, ibid. 2 1 , 260 (1888); Gesellschaft Chim. Ind, Basel, German Patent 379003 (1921); Swiss priority (1920); Farbenfabriken Bayer A G , German Patent 400242 (1920); German Patent 409783 (1921); C.

C-SH1 II II s s 8 hrs • boiling X — > O'' ^ N-C-CH,-C-N^ I s I s J R = C H , - C H t - C H 8- ^0 N - / The susceptibility to attack displayed by the vinyl group is also illus­ trated by the conversion of vinylpyrrolidone into N-thioacetylpyrrolidone (111b) (Example 31a). I 1 ^ Lo + S N CH=CH, 8 hrs 165° > I I l J=o N S=C CH8 Acetylene in the presence of secondary amines readily undergoes a double attack by sulfur in the absence of water to give dithiooxalamides (113) (Example 32). No other data appear to exist regarding the degra­ dation by sulfur on both sides.

22) J. A. King and F. H . McMillan, J. Am. Chem. Soc. 68, 632 (1946). (23) D. B. Pattison and M . Carmack, J. Am. Chem. Soc. 68, 2033 (1946). (24) R. T. Gerry and E. V. Brown, J. Am. Chem. Soc. 75, 740 (1953). (25) D. Nightingale and R. A. Carpenter, / . Am. Chem. Soc. 71, 3560 (1949). (26) C. Willgerodt and F. H . Merk, J. prakt. Chem. 80, 192 (1909). (27) Cf. also R. T. Arnold, E. Schultz, and H . Klug, / . Am. Chem. Soc. 66, 1606 (1944). (28) J. A. King and F. H. McMillan, J. Am. Chem. Soc.

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