Solvolyses of 1-14C-2-phenylethyl tosylate (1-OTs-1-14C) were carried out in HOAc and H2O solvent systems with or without added NaN3. In the absence of added azide ion, the products obtained from a given solvent mixture of HOAc–H2O, 1-OAc-14C, and 1-OH-14C, showed essentially the same extent of rearrangement of the 14C-label from C-1 to -2. In the presence of added azide ion, the rearrangement in the 1-N3-14C was less than that found in the 1-OAc-14C or 1-OH-14C. The results are interpreted in terms of concurrent direct displacement to give product and product formation from the ethylenephenonium ion.

2-Phenylethyl triflate (1-OTf) was synthesized by the reaction of AgOTf with 2-phenylethyl iodide (1-I) in cyclohexane as solvent. However, when 1-14C-2-phenylethyl iodide (1-I-1-14C) was used as a reactant, the resulting 1-OTf-14C showed an essentially complete scrambling of the 14C-label over the C-1 and -2 positions. Similar reactions of 1-I-1-14C with AgOTs and with AgOAc gave 1-OTs-14C and 1-OAc-14C with, respectively, about 49 and 11% rearrangement of the label from C-1 and -2.

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Die Umsetzung des Jodids (I) mit Ag‐triflat (II) führt zum Triflat (III).

Die Solvolyse des Tosylats (I) mit Wasser/Essigsäure‐Gemischen wechselnder Zusammensetzung führt zu den Solvolyseprodukten (III) und (IV) sowie in Anwesenheit von Na‐azid zu der zusätzlichen Bildung von 2‐Phenyl‐äthylazid.