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.
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.
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