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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 1, 1971 - Issue 2
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Original Articles

Reaction of Aliphatic Diazo Compounds with Dinitrogen Trioxide. A Facile route to 3,4-Disubstituted 1,2,5-Oxadiazole-2-oxides(Furoxans)

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Pages 121-124 | Published online: 03 Jan 2007

References

  • Engberts , J. B. F. N. and Zuidema , G. 1970 . Rec. Trav. Chim. , 89 : 741
  • Lunge , G. Ber. . 11, 1229. 1641 . 1878 .
  • Brown , J. F. Jr. 1955 . J. Am. Chem. Soc. , 77 : 6341
  • Furoxan VII could also be obtained in high yield from the reaction of ethyl diazoacetate either with liquid N2O3 at -70° or with N2O3 in CH2Cl2 at -70°. ∗Reactions of N2O3, with olefins have been interpreted both in terms of hemolytic or heterolytic processes. 10
  • Farrar , W. V. 1964 . J. Chem. Soc. , : 904
  • van Leusen , A. M. and Strating , J. 1970 . Quart. Rep. Sulfur Chem. , 5 : 67 3, 4 Diarylsuflyonyl- and 3, 4-dialkylsulfonylfuroxans have also been obtained as byproducts in the reaction of α-diazosulfones with NOCl (i. e. R = p-CH3C6H4SO2, 27% R= C6H5CH2SO2, R = 11%; R = (CH3)3 CSO211%). A. M. van Leusen, J. C. Jagt and Miss G. H. J, van Buuren, personal communication. See also
  • Kaufman , J. V. R. and Picard , J. P. 1959 . Chem. Rev. , 59 : 429
  • Daniewski , A. R. and Urbanski , T. 1963 . Rocz. Chem. , 42 : 289
  • Wieland , H. and Reissenegger , K. 1913 . Ann. , 401 : 244
  • Snechter , H. 1964 . Rec. Chem. Progress , 25 : 55
  • Grundman , C. 1970 . The Cheolstr7 of the cyano group , Edited by: Rappoport , Z. 791 New York, N. Y. : Intersc. Publ. .
  • Compare: J. B. F. N. Engberts and 3. Zwanenburg, Tetrahedron Letters 1967, 831
  • Novikow , S. S. , Lebedev , O. V. , Khmelnitskii , L. J. and Egorov , Y. P. 1958 . Zhur. Obshchei. Khim. , 28 : 2305 C. A. 53, 4112 (1959)

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