The gas-phase Smiles rearrangement the effect of ring substitution. An 18O labelling study

✍ Scribed by Peter C. H. Eichinger; John H. Bowie

• Book ID: 102558548
• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: English
• Weight: 391 KB
• Volume: 27
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/oms.1210271007

✦ Synopsis

The gas-phase Smiles reaction of RC,H,O(CH,),O-(n = 2 or 3) is an ips0 rearrangement which is strongly influenced by the nature of the substituent R. Electron-withdrawing groups enhance the rearrangement. When the substituent R is halogen or MeO, and occupies the ortho position, ortho cyclization competes with the Smiles rearrangement.