5-Methyl-5-nitrosohexan-2-one, reexamined

Arkivoc

Volumn 2001, Issue 5, 2001, Pages 36-41

  Rettenbacher, Arno S ^a   Schantl, Joachim G ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

Aliphatic nitro; Aluminum amalgam reduction; Hydroxylamino; Mercuric oxide oxidation; Nitroso compounds

Indexed keywords

5 METHYL 5 NITROSOHEXAN 2 ONE; ALKANONE; DIMER; UNCLASSIFIED DRUG;

ARTICLE; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 3242737734     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. Boyer, J. H. in Feuer, H. The Chemistry of the Nitro and Nitroso Groups, pt. 1; Wiley, New York, 1969, p. 278.
2. Marsden, H. M.; Shreve, J. M. J. Fluorine Chem. 1985, 27, 275-284.
3. Rettenbacher, A.R. Doctoral Thesis, University of Innsbruck, 2001.
4. Konopski, L. Org. Mass. Spectrom. 1990, 25, 204-208.
5. Ballini, R.; Bosica, G. Tetrahedron Lett. 1996, 37, 8027-8030.
6. Napolitano, E.; Fiaschi, R.; Mastrorilli, E. Synthesis 1986, 122-125.
7. Calder, A.; Forrester, A. R.; Hepburn, S. P. Org. Synth. 1972, 52, 77-82.
8. Originally,4 sodium hypobromite has been employed for the oxidation of 3; yellow or red mercuric oxide proved to be a more convenient oxidation reagent providing a higher yield of 4a.
9. Reported overall yield:4 26%.
10. 3 solution different monomer/dimer ratios have been reported.4 4/4a 70:30, 5/5a 35:65; it is not clear if these figures refer to equilibrium conditions.
11. Feuer, H.; Miller, R. J. Org. Chem. 1961, 26, 1348-1357.
12. 13C correlation cross-peak was observed at 2.36/29.
13. p-Toluenesulfonic acid monohydrate was dehydrated at 100 °C for 1 h.
14. Equilibrium ratio.
15. 13C signals were detectable only with a freshly prepared solution of the dimer 4a or 5a before the equilibrium shifted to the predominant monomer 4 or 5, respectively.