An improved oxidation method for the synthesis of azodicarbonyl compounds

Synthetic Communications

Volumn 27, Issue 18, 1997, Pages 3197-3200

  Starr, Jeremy T ^a   Rai, Gurdev S ^a   Dang, Hung ^a   McNelis, Brian J ^a  

^a SANTA CLARA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZODICARBONYL; DIBENZYL AZODICARBOXYLATE; IODOBENZENE; N BROMOSUCCINIMIDE; NITRIC ACID; NITROGEN DIOXIDE; PHENYL IODOSOACETATE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; DATA ANALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; OXIDATION;

EID: 0030814712     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708004179     Document Type: Article

References (10)

1. Other Oxidation Methods: a) Leblanc, Y.; Mitchell, H. J. Org. Chem. 1994, 59, 628. b) Little, R.D.; Venegas, M.G. Org. Syn. 1983, 61, 17. c) Brimble, M.A.; Heathcock, C.H.; Nobin, G.N. Tetrahedron Asymmetry 1996, 7, 2007. d) Vederas, J.C.; Harris, J.M; Bolessa, E.A.; Mendonca, A.J.; Feng, S. J. Chem. Soc. Perkin Trans. 1 1995, 1945. e) Moriarty, R.M.; Prakash, I.; Penmasta, R. Synth. Commun. 1987, 17, 409. f) Loew, F.S.; Weiss, C.D. J. Heterocycl. Chem. 1976, 13, 829.
2. Other Oxidation Methods: a) Leblanc, Y.; Mitchell, H. J. Org. Chem. 1994, 59, 628. b) Little, R.D.; Venegas, M.G. Org. Syn. 1983, 61, 17. c) Brimble, M.A.; Heathcock, C.H.; Nobin, G.N. Tetrahedron Asymmetry 1996, 7, 2007. d) Vederas, J.C.; Harris, J.M; Bolessa, E.A.; Mendonca, A.J.; Feng, S. J. Chem. Soc. Perkin Trans. 1 1995, 1945. e) Moriarty, R.M.; Prakash, I.; Penmasta, R. Synth. Commun. 1987, 17, 409. f) Loew, F.S.; Weiss, C.D. J. Heterocycl. Chem. 1976, 13, 829.
3. Other Oxidation Methods: a) Leblanc, Y.; Mitchell, H. J. Org. Chem. 1994, 59, 628. b) Little, R.D.; Venegas, M.G. Org. Syn. 1983, 61, 17. c) Brimble, M.A.; Heathcock, C.H.; Nobin, G.N. Tetrahedron Asymmetry 1996, 7, 2007. d) Vederas, J.C.; Harris, J.M; Bolessa, E.A.; Mendonca, A.J.; Feng, S. J. Chem. Soc. Perkin Trans. 1 1995, 1945. e) Moriarty, R.M.; Prakash, I.; Penmasta, R. Synth. Commun. 1987, 17, 409. f) Loew, F.S.; Weiss, C.D. J. Heterocycl. Chem. 1976, 13, 829.
4. Other Oxidation Methods: a) Leblanc, Y.; Mitchell, H. J. Org. Chem. 1994, 59, 628. b) Little, R.D.; Venegas, M.G. Org. Syn. 1983, 61, 17. c) Brimble, M.A.; Heathcock, C.H.; Nobin, G.N. Tetrahedron Asymmetry 1996, 7, 2007. d) Vederas, J.C.; Harris, J.M; Bolessa, E.A.; Mendonca, A.J.; Feng, S. J. Chem. Soc. Perkin Trans. 1 1995, 1945. e) Moriarty, R.M.; Prakash, I.; Penmasta, R. Synth. Commun. 1987, 17, 409. f) Loew, F.S.; Weiss, C.D. J. Heterocycl. Chem. 1976, 13, 829.
5. Other Oxidation Methods: a) Leblanc, Y.; Mitchell, H. J. Org. Chem. 1994, 59, 628. b) Little, R.D.; Venegas, M.G. Org. Syn. 1983, 61, 17. c) Brimble, M.A.; Heathcock, C.H.; Nobin, G.N. Tetrahedron Asymmetry 1996, 7, 2007. d) Vederas, J.C.; Harris, J.M; Bolessa, E.A.; Mendonca, A.J.; Feng, S. J. Chem. Soc. Perkin Trans. 1 1995, 1945. e) Moriarty, R.M.; Prakash, I.; Penmasta, R. Synth. Commun. 1987, 17, 409. f) Loew, F.S.; Weiss, C.D. J. Heterocycl. Chem. 1976, 13, 829.
6. Other Oxidation Methods: a) Leblanc, Y.; Mitchell, H. J. Org. Chem. 1994, 59, 628. b) Little, R.D.; Venegas, M.G. Org. Syn. 1983, 61, 17. c) Brimble, M.A.; Heathcock, C.H.; Nobin, G.N. Tetrahedron Asymmetry 1996, 7, 2007. d) Vederas, J.C.; Harris, J.M; Bolessa, E.A.; Mendonca, A.J.; Feng, S. J. Chem. Soc. Perkin Trans. 1 1995, 1945. e) Moriarty, R.M.; Prakash, I.; Penmasta, R. Synth. Commun. 1987, 17, 409. f) Loew, F.S.; Weiss, C.D. J. Heterocycl. Chem. 1976, 13, 829.
7. Previous syntheses of compounds 2, 4 and 5: a) 2, reference 1c and d. b) 4, Ullrich, J.; Boshagen, H. Chem. Ber. 1959, 92, 1478. c) 5, reference 1b.
8. Previous syntheses of compounds 2, 4 and 5: a) 2, reference 1c and d. b) 4, Ullrich, J.; Boshagen, H. Chem. Ber. 1959, 92, 1478. c) 5, reference 1b.
9. Previous syntheses of compounds 2, 4 and 5: a) 2, reference 1c and d. b) 4, Ullrich, J.; Boshagen, H. Chem. Ber. 1959, 92, 1478. c) 5, reference 1b.
10. Bleach (NaOCl) also gave a complex mixture of products.