The behavior of (α-hydroxy)-cyclopropylcarbinyl free radicals

✍ Scribed by Douglas C. Neckers

• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 279 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)90146-1

✦ Synopsis

The unique ability of certa3n neighboring groups to facilitate carboniun Ion fomatlon has stimulated significant research effort and socontroversy (I). In the fonaationof free radidl inter6mdiata6, mighboring groups are much 1066 effective. Theonlyluge-ighboringgrcap effects am obssrvsd for wlecul6s po6se66ing heavy at.0166 (2) and (3). Ofparticul$r i.ntere6taretho60 Carbcni~ions OcntAining neighboring cyclopropyl groups. Roberts and coworkers have postulated, on the basis of kinetic and product isclatlcn evidence, that the bicyclcbutcnl~ ion (I) Is rsspcnslbls for the increased stability of the cyclopropylcarblnylsystemandtbatrearrangedpmducts resultbecause of itslntmmdlacy.