Croatica Chemica Acta, Vol. 65 No. 3, 1992.
Original scientific paper
On a New Mechanism of S-O Scission in the Solvolysis of Aryl Triflates
Takaaki Sonoda
; Research Institute of Industrial Science, Kyushu University, Kasuga Sakamoto, Fukuoka 816, Japan
Antonio Garcia Martinez
; Departamento Quimica Orgánica, Facultad de Ciencias Quimicas, Univesidad Complutense, E-28040 Madrid, Spain
Michael Hanack
; Institut für Organische Chemie der Universitàt Tübingen, Auf der Morgenstelle 18, D-7400 Tübingen, Germany
L. R. Subramanian
; Institut für Organische Chemie der Universitàt Tübingen, Auf der Morgenstelle 18, D-7400 Tübingen, Germany
Abstract
The solvolysis of 3,3-di-tert-butyl-4-hvdroxyphenyl triflate (7) in tri- fluoroethanol buffered with the non-nucleophilic base, 2,G-di-tert-butyl-4-methylpyridine proceeds surprisingly fast. This phenomenon is explained by a new type of elimination of triflinate anion from the conjugate base 10 of the triflate 7 to form 2,6-di-tert-butyl-1,4-benzoquinone.
Keywords
Hrčak ID:
137119
URI
Publication date:
15.10.1992.
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