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The gas‐phase Smiles rearrangement the effect of ring substitution. An 18 O labelling study
Author(s) -
Eichinger Peter C. H.,
Bowie John H.
Publication year - 1992
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210271007
Subject(s) - smiles rearrangement , substituent , labelling , ring (chemistry) , gas phase , chemistry , halogen , cope rearrangement , stereochemistry , substitution (logic) , medicinal chemistry , organic chemistry , philosophy , linguistics , biochemistry , alkyl
The gas‐phase Smiles reaction of RC 6 H 4 O(CH 2 ) n O − ( n = 2 or 3) is an ipso 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.