Rearrangement Studies with 14C. XXXVI. Solvolysis of 1-14C-2-Phenylethyl Tosylate in Aqueous Acetic Acid with or without Added Sodium Azide

Solvolyses of 1- 14 C-2-phenylethyl tosylate (1-OTs-1- 14 C) were carried out in HOAc and H 2 O solvent systems with or without added NaN 3 . In the absence of added azide ion, the products obtained from a given solvent mixture of HOAc-H 2 O, 1-OAc- 14 C, and 1-OH- 14 C, showed essentially the same...

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Bibliographic Details
Published in:Canadian journal of chemistry 1972-05, Vol.50 (9), p.1371-1375
Main Authors: Lee, C. C, Unger, D, Vassie, Sharon
Format: Article
Language:English
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Summary:Solvolyses of 1- 14 C-2-phenylethyl tosylate (1-OTs-1- 14 C) were carried out in HOAc and H 2 O solvent systems with or without added NaN 3 . In the absence of added azide ion, the products obtained from a given solvent mixture of HOAc-H 2 O, 1-OAc- 14 C, and 1-OH- 14 C, showed essentially the same extent of rearrangement of the 14 C-label from C-1 to -2. In the presence of added azide ion, the rearrangement in the 1-N 3 - 14 C was less than that found in the 1-OAc- 14 C or 1-OH- 14 C. The results are interpreted in terms of concurrent direct displacement to give product and product formation from the ethylenephenonium ion.
ISSN:0008-4042
1480-3291
DOI:10.1139/v72-214