Free radical-mediated ring expansion reactions: Endocyclic cleavage of cyclopropylcarbinyl radicals

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Ring expansion reactions via endocyclic cleavage of cyclopropylcarbinyl radicals derived from the reaction of [1 -benzyloxycarbonylbicyclo[n.1.0]alk-(n+1)-yl]-1-imidazolethiocarboxylates with tributyltin hydride/AIBN proceeded to produce 3-cycloalkenecarboxylates in good yields. Benzyl (5 '-phenoxypentyl)-3-cyclohepten-1-carboxylate was obtained in 33% yield from the reaction of benzyl 5-methylenebicyclo[4.1.0]-1-carboxylates with 4-phenoxybutyl iodide under radical conditions. Selective cleavage of endocyclic bond in cyclopropane to the cyclohexane, results from stabilization of the resultant radical by the carbonyl groups, such as the benzyloxycarbonyl group, which lower the transition state energy for the final cyclopropane cleavage in the ring expansion.
Publisher
KOREAN CHEMICAL SOC
Issue Date
2000-06
Language
English
Article Type
Article
Keywords

ELECTRON-TRANSFER; GROUP MIGRATION; BETA-FISSION; REARRANGEMENT; FRAGMENTATION; CYCLOPROPANES; KETONES; SYSTEM; ALKYL; CYANO

Citation

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.21, no.6, pp.595 - 603

ISSN
0253-2964
URI
http://hdl.handle.net/10203/75495
Appears in Collection
CH-Journal Papers(저널논문)
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