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Mechanism of the rearrangement of 2-(vinyloxy)alkyl to 4-ketobutyl radicals

✍ Scribed by David Crich; Qingwei Yao

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
622 KB
Volume
50
Category
Article
ISSN
0040-4020

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✦ Synopsis

The rearrangement of Z(vinyloxy)alkyl to 4-ketobutyl radicals has been demonstrated b proceed by a two step mechanism involving initial 5-endo-trigoual cyclii 10 give a tetrahydrof~yl radical which thtn fragments to the final radical. Fragmentation of the tetrahydrofrwnyl radicals is demonstrated by their genetation from the corresponding 2-(&ylthio)-tetrahydmfurans with stanmmesandAIBN. 'Ihereanangementmactionis completely blocked when the intermediate tetrahdrofuranyl radical is set up to undergo a Mexenyl rearrangement We are interested in the study of a class of free radical rearrangements that may be conveniently generalized by the formalism of Scheme 1. NY\ 2 x, Path a pyxx Path b z4yxx \ B-A* -.B-#( -;-A*

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Rearrangement of 2,4-di-mpentadienals IVa-d was described as a consequence of the successive alkyl substitutions on the C-2 and C-4 positions. 1 H-FT nmr spectroscopy suggested that the reaction involves ketene VI&& as an intermediate. Hydrogen-hydrogen repulsive interactions occurred in annulenes (