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Title :Mn(III)-BASED OXIDATIVE RADICAL RING-EXPANSION REACTION USING SQUARATE DERIVATIVES : SELECTIVE SYNTHESIS OF BIS(BUTENOLIDE)S AND THE ACETATE MONOMERS
Authors :Sasaki, Jun-ichi
Kobayashi, Makoto
Ibe, Yusuke
Nishino, Hiroshi
Issue Date :Sep-2019
Citation jtitle :Heterocycles
vol. :99
no. :2
start page :958
end page :988
Abstract :The Mn(III)-based oxidation of phenyl- and alkyl-substituted hydroxycyclobutenones selectively produced the bis(butenolide)s or the acetate monomers via the 5-endo radical cyclization depending upon the concentration of the reaction. A similar reaction of hydroxycyclobutenones bearing an alkenyl and alkynyl substituent did not produce any bis(butenolide)s or acetate monomers, but the 5-exo and 6-endo radical cyclization products including the unsaturated group. The oxidation of the hydroxycyclobutenones having an unsaturated substituent in the presence of alkenes afforded radical coupling products during the 5-exo radical cyclization. The reaction details, structure determination of the products, and the mechanism for the formation of the products are described.
URL :https://www.heterocycles.jp/newlibrary/libraries/abst/25802
Type Local :雑誌掲載論文
ISSN :18810942
Publisher :The Japan Institute of Heterocyclic Chemistry
Rights :© 2019 The Japan Institute of Heterocyclic Chemistry
URI :http://hdl.handle.net/2298/42462
Appears in Collections:Journal Article (Sciende)
Please use this identifier to cite or link to this item: http://hdl.handle.net/2298/42462