The O-neophyl rearrangement of 1,1-diarylalkoxyl radicals. Experimental evidence for the formation of an intermediate 1-oxaspiro[2,5]octadienyl radical

TETRAHEDRON LETTERS

卷:51

Article

Bietti, Massimo¹  Calcagni, Alessandra¹  Cicero, Daniel Oscar¹  Martella, Roberto¹  Salamone, Michela¹ 

[1] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, I-00133 Rome, Italy

关键词: Alkoxyl radical;    O-Neophyl rearrangement;    Cyclopropylcarbinyl radical;    Ring-opening;   

DOI  :  10.1016/j.tetlet.2010.05.149

来源: Elsevier

【 摘 要 】

A product study on the reactivity of a 1,1-diarylalkoxyl radical bearing 2,2-diphenylcyclopropyl groups in the para-positions has been carried out. The exclusive formation of a product deriving from cyclopropyl ring-opening has been observed, indicating that 1,1-diarylalkoxyl radicals exist in equilibrium with a bridged 1-oxaspiro[2,5]octadienyl radical. This represents the first experimental evidence in support of the stepwise nature of the O-neophyl rearrangement of 1,1-diarylalkoxyl radicals. (C) 2010 Elsevier Ltd. All rights reserved.

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