The reactivity of cumyloxyl radicals bearing cyclopropyl and 2,2-diphenylcyclopropyl groups in the para position has been investigated. Depending on radical structure, products deriving from C-C beta-scission and/or cyclopropyl ring-opening are observed, supporting the hypothesis that cumyloxyl (and, more generally, arylcarbinyloxyl) radicals exist in equilibrium with 1-oxaspiro[2,5]octadienyl radicals, in full agreement with the previously proposed mechanism for the O-neophyl rearrangement of 1,1-diarylalkoxyl radicals.
Salamone, M., Bietti, M., Calcagni, A., Gente, G. (2009). Phenyl Bridging in Ring-Substituted Cumyloxyl Radicals. A Product and Time-Resolved Kinetic Study. ORGANIC LETTERS, 11(11), 2453-2456 [10.1021/ol900635z].
Phenyl Bridging in Ring-Substituted Cumyloxyl Radicals. A Product and Time-Resolved Kinetic Study
SALAMONE, MICHELA;BIETTI, MASSIMO;
2009-01-01
Abstract
The reactivity of cumyloxyl radicals bearing cyclopropyl and 2,2-diphenylcyclopropyl groups in the para position has been investigated. Depending on radical structure, products deriving from C-C beta-scission and/or cyclopropyl ring-opening are observed, supporting the hypothesis that cumyloxyl (and, more generally, arylcarbinyloxyl) radicals exist in equilibrium with 1-oxaspiro[2,5]octadienyl radicals, in full agreement with the previously proposed mechanism for the O-neophyl rearrangement of 1,1-diarylalkoxyl radicals.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
