Structure and chemistry of acetoxybenziodazole. Acid-catalyzed rearrangement of benziodazoles to 3-iminobenziodoxoles

Journal of the American Chemical Society

Volumn 119, Issue 31, 1997, Pages 7408-7409

  Zhdankin, Viktor V ^a   Arbit, Ruslan M ^a   McSherry, Marc ^a   Mismash, Brian ^a   Young Jr , Victor G ^b  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

^b University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOIODINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 0030740842     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971606z     Document Type: Article

References (17)

1. (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997. Varvoglis, A. Tetrahedron 1997, 53, 1179.
2. (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997. Varvoglis, A. Tetrahedron 1997, 53, 1179.
3. (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997. Varvoglis, A. Tetrahedron 1997, 53, 1179.
4. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
5. (c) Koser G. F. In The Chemistry of Functional Groups, Suppl. D; Patai, S., Rappoport, Z., Eds.; Wiley-Interscience: Chichester, U.K., 1983; Chapter 18, pp 721-811.
6. Wolf, W.; Steinberg, L. J. Chem. Soc., Chem. Commun. 1965, 449.
7. Moss, R. A.; Chatterjee, S.; Wilk, B. J. Org. Chem. 1986, 51, 4303.
8. Barber, H. J.; Henderson, M. A. J. Chem. Soc. (C) 1970, 862.
9. Akai, S.; Okuno, T.; Egi, M.; Takada, T.; Tohma, H.; Kita, Y. Heterocycles 1996, 42, 47.
10. Balthazar, T. M.; Godaz, D. E.; Stults, B. R. J. Org. Chem. 1979, 44, 1447. Naae, D. G.; Gougoutas, J. Z. J. Org. Chem. 1975, 40, 2129.
11. Balthazar, T. M.; Godaz, D. E.; Stults, B. R. J. Org. Chem. 1979, 44, 1447. Naae, D. G.; Gougoutas, J. Z. J. Org. Chem. 1975, 40, 2129.
12. 2 factor = 0.0517. Further details on crystal structures of 4 and 7c are available in the Supporting information.
13. 4O: C, 29.19; H, 1.75; N, 19.45. Found: C, 29.28; H, 1.72; N, 19.35. CAUTION: Azidobenziodazole 5 decomposes with an explosion upon heating to 122 °C and should be handled with care.
14. Zhdankin, V. V.; Krasutsky, A. P.; Kuehl, C. J.; Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz, J. T. J. Am. Chem. Soc. 1996, 118, 5192.
15. Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115, 9347. Magnus, P.; Hulme, C.; Weber, W. J. Am. Chem. Soc. 1994, 116, 4501.
16. Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115, 9347. Magnus, P.; Hulme, C.; Weber, W. J. Am. Chem. Soc. 1994, 116, 4501.
17. 3CN in an open air container.