Nitroxyl Radical Addition to Pentafulvenones Forming Cyclopentadienyl Radicals: A Test for Cyclopentadienyl Radical Destabilization

…, J Porter, D Tahmassebi, TT Tidwell

Index: Allen; Porter; Tahmassebi; Tidwell Journal of Organic Chemistry, 2001 , vol. 66, # 22 p. 7420 - 7426

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Citation Number: 15

Abstract

Photochemical Wolff rearrangements in alkane solvents of the 6-diazo-2, 4- cyclohexadienones 4 and 13-15 give pentafulvenone (1), 2, 3-benzopentafulvenone (2), dibenzopentafulvenone (3), and 2, 4-di-tert-butylpentafulvenone (16), as identified by conventional UV and IR spectroscopy. Reactions of these fulvenyl ketenes with tetramethylpiperidinyloxyl (TEMPO) proceed by addition of TEMPO to the carbonyl carbon ...