Nitroxyl Radical Reactions with 4-Pentenyl-and Cyclopropylketenes: New Routes to 5-Hexenyl-and Cyclopropylmethyl Radicals

…, MF Fenwick, H Henry-Riyad, TT Tidwell

Index: Allen; Fenwick; Henry-Riyad; Tidwell Journal of Organic Chemistry, 2001 , vol. 66, # 17 p. 5759 - 5765

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Citation Number: 39

Abstract

4-Pentenylketenes 4a and 9 and cyclopropylketenes 3a, 13, 14 (RCH CO) are generated by photochemical Wolff rearrangements and observed by IR as relatively long-lived species at room temperature in hydrocarbon solvents. The reactions of these ketenes with the nitroxyl radicals tetramethylpiperidinyloxyl (TEMPO, TO) and tetramethylisoindoline-2-oxyl (TMIO, IO) form carboxy substituted 5-hexenyl and cyclopropylmethyl radicals which are either ...