The gas-phase Smiles rearrangement: a heavy atom labeling study

PCH Eichinger, JH Bowie…

Index: Eichinger, Peter C.H.; Bowie, John H.; Hayes, Roger N. Journal of the American Chemical Society, 1989 , vol. 111, # 12 p. 4224 - 4227

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Citation Number: 44

Abstract

Abstract: Heavy atom (I3C and lSO) labeling shows that the product ion PhO-from PhO (CH2) 20-and products PhO-and PhS-from PhS (CH2) 20-are formed through Smiles intermediates I (X= Y= 0 or X= 0, Y= S). The analogous product ions from PhO (CH2) 30-and PhS (CH,), O-are formed by two processes. It is likely that these are (i) Smiles and (ii) SNi attack by 0-at the methylene group PhXCH2. The extent of the Smiles process decreases ...