Hydrogen abstraction from unactivated hydrocarbons using a photochemically excited isoindoline nitroxide

Chemistry Letters

Volumn , Issue 9, 1997, Pages 857-858

  Bottle, Steven E ^a   Chand, Ugesh ^a   Micallef, Aaron S ^a  

^a QUEENSLAND UNIVERSITY OF TECHNOLOGY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031317078     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.857     Document Type: Article

References (11)

1. J.F.W. Keana, R.J. Dinerstein, and F. Baitis, J. Org. Chem., 36(1), 209(1971).
2. b) L.J. Johnston, M. Tencer, and T.A. Scaiano, J. Am. Chem. Soc., 97(3), 648(1975).
3. A.L.J. Beckwith, V.W. Bowry, and K.U. Ingold, J. Am. Chem. Soc., 114, 4983(1992).
4. b) V.W. Bowry, and K.U. Ingold, J. Am. Chem. Soc., 114, 4992(1992).
5. c) S.R. Harrison, R.S. Pilkington, and L.H. Sutcliffe, J. Chem. Soc., Faraday Trans. I, 80, 669 (1984).
6. The hydroxylamine by-products are rapidly reoxidised by adventitious oxygen to reform 1 during the experiment and work up.
7. GC/MS of the reaction mixture gave a peak with m/z = 175 attributable to 8 and 9 was isolated from the reaction mixture and fully characterised.
8. J.P. Bartley, W.K. Busfield, I.D. Jenkins, and S. Thang, Organic Mass Spectrom., 23, 739(1988).
9. All yields reported are for isolated products at high conversion and are based on actual nitroxide consumed. Greater yields (HPLC determined) could be obtained at lower conversions. All products were susceptible to some degree of secondary photodegradation (especially 5) and isolated ratios reflect this. All compounds were identified by NMR and mass spectrometry and satisfactory elemental analyses were obtained for all new compounds.
10. The comixtures of 4/5 and 6/7 could not be completely separated by preparative HPLC. Yields were calculated from analytical HPLC and supported by NMR integration of the isolated mixtures.
11. R.D. Grant, P.G. Griffiths, G. Moad, E. Rizzardo, and D.H. Solomon, Aust. J. Chem., 44, 1407(1991).