Synthesis of C-Sulfonylcarbohydroximoyl Chlorides from α-Diazosulfones and Nitrosyl Chloride¹

References

• van Leusen , A. M. , Strating , J. and van Leusen , Daan . 1973 . : 5207 Chemistry of a-Diazosulfones, Part 16; Part15, Tetrah. Letters
   Google Scholar
• vanLeusen , A. M. and Strating , J. 1970 . Quart. Rep. Sulfur Chem. , 2 ( 67 )
   Google Scholar
• Zwanenburg , B. , Midde1bos , W. , Hemke , G. J.K. and Strating , J. 1971 . Recl. Trav. Chim. Pays-Bas , 90 : 429
   Google Scholar
• Middelbos , W. private communication
   Google Scholar
• Weygand , F. and Bestmann , H. J. 1961 . Neuere Methoden der präparativen organischen Chemie , Edited by: Foerst , W. Vol. Band III , 280 Weinheim : Verlag Chemie .
   Google Scholar
• Seth , U. S. and Deshapande , S. S. 1952 . J. Indian Chem. Soc. , 29 : 539 R. P. Kapoor, K. C. Gupta, S. M. Gupta, Agra Univ. J. Res. 10(2), 1 (1961), cf. Chem. Abstr. 58, 2442d (1963); Likewise, perfluoroalkyldiazomethanes and nitrosyl chloride give RFC(Cl)=NOH, L. W. Kissinger, W. E. McQuistion, M. Schwartz and L. Goodman, Tetrahedron 19, Suppl. 1, 131 (1963)
   Google Scholar
• van Leusen , A. M. , Iedema , A. J. W. and Strating , J. Chem. Comm. , 1968 440
   Google Scholar
• Barbaro , G. , Battaglia , A. and Dondoni , A. J. Chem. Soc. B , 1970 588
   Google Scholar
• Farrar , W. V. J. Chem. Soc. , 1964 904
   Google Scholar
• Engbersen , J. F. J. and Engberts , J. B. F. N. 1971 . Synth. Comm. , 1 : 121
   Google Scholar
• Huisgen , R. , Grashey , R. and Sauer , J. 1964 . The Chemistry of Alkenes , Edited by: Patai , S. 739 New York : Interscience . cf.
   Google Scholar
• Grundmann , C. and Frommeld , H. D. 1965 . J. Org. Chem. , 30 : 2077 For precedence of the conversion of nitrile oxides to nitriles by tertiary phosphines or phosphites, see, for a similar conversion of hydroximoyl chlorides to nitriles, see T. Sasaki and T. Yoshioka, Bull. Chem. Soc. Japan 41, 2206 (1968). We, in our reaction, were neither successful by using triphenyl-phosphine or triethyl phosphite in combination with triethylamine
   Google Scholar
• van Leusen , A. M. and Jagt , J. C. Tetrah. Letters , 1970 967
   Google Scholar
• Cox , J. M. and Ghosh , F. P. Tetrah. Letters , 1969 3351
   Google Scholar
• During this work we were able to show that furoxan 5a can be deoxygenated, in contrast to a previous report by Farrar9a, to 3,4-ditosyl-1,2,5-oxadiazole (62% yield, mp 119–120°) with triethyl phosphite in refluxing benzene
   Google Scholar
• Otto , R. 1889 . J. Prakt. Chem. [2] , 40 : 526
   Google Scholar