A new method for the generation and capture of iminyl radicals

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4531-4534

  Boivin, Jean ^a   Schiano, Anne Marie ^a   Zard, Samir Z ^a,b   Zhang, Haiwen ^b  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ESTER; RADICAL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0033546251     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00720-0     Document Type: Article

References (26)

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26. 13. Typical experimental procedure: a solution of oxime ester (1 mmole) in 2-propanol is added over one hour to a refluxing suspension of nickel powder (1.9g; 30eq.) in a mixture of 2-propanol (7.7 ml) and acetic acid (3.3 ml). Refluxing under an inert atmosphere was continued until thin layer chromatograghic analysis indicated essentially complete reaction (2-3 hours). For the synthesis of compounds 18 and 19, diphenyl diselenide (2 eq.) and allyl tolylsulfone (10 eq.) were respectively added with the nickel at the beginning of the experiment. The reaction mixture was then filtered through Celite, diluted with water (20ml), neutralised with sodium bicarbonate, and finally extracted with ether. The organic layer was dried, concentrated, and the residue purified by flash chromatography. Compounds 7,15,17 were identical to authentic samples prepared previously by another route to iminyl radicals (ref. 4). Compound 21 is known in the literature (Gawley, R. E.; Termine, E. J.; Onan, K. D. J. Chem. Soc., Chem. Commun. 1981, 568-569); as for the others (13, 18, 19, 23, 24, 26), their relatively simple structure was easily established by the usual spectroscopic techniques and gave correct microanalyses or high resolution MS.