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Synthesis 1995; 1995(10): 1278-1282
DOI: 10.1055/s-1995-4097
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Synthesis of Lipophilic 3,4-Disubstituted 2,5-Dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxyl Radicals

Tamás Kálai, Nóra M. Bárácz, Gyula Jerkovich, Olga H. Hankovszky, Kálmán Hideg*
  • *Central Research Laboratory, Chemistry, University of Pécs, H-7643 Pécs, P.O. Box 99, Hungary, Fax +36(72)326244; E-mail KHIDEG@main.pote.hu
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Publication Date:
31 December 2000 (online)

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The Grignard reaction of the esters 2a, b with octylmagnesium bromide proceeds through an allylic rearrangement to give the 3-methylene-4-octyl radical 3. Bromination of its O-acetyl derivative 5 gives allylic bromides 6 and 7 as key intermediates toward lipophilic spin labels.

Grignard reaction - allylic rearrangement - spin labelling - SH labels - oxaoleic acid

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