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 ...
[Barton, Derek H. R.; Csuhai, Eva; Doller, Dario; Balavoine, Gilbert Journal of the Chemical Society, Chemical Communications, 1990 , # 24 p. 1787 - 1789]
