7087-36-7Relevant articles and documents
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Posner,G.H. et al.
, p. 1373 - 1376 (1975)
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Regioselective radical cyclization initiated by the reaction of allylic hydroperoxides with iron(II) sulfate
Masuyama, Araki,Sugawara, Tomohiro,Nojima, Masatomo,McCullough, Kevin J.
, p. 353 - 366 (2007/10/03)
Treatment of 1-methyl-2-methylene-1-cyclohexyl hydroperoxide with a mixture of FeSO4/CuCl2 yielded 1-(1-chlorocyclohexyl)ethanone as the major product consistent with 6-endo-trig cyclization of the intermediate 5-acetylhex-5-enyl rad
Cyclizations of ω-Allenyl Radicals
Apparu, Marcel,Crandall, Jack K.
, p. 2125 - 2130 (2007/10/02)
Allenyl halides of structure (CH3)2C=C=CH(CH2)nX with n=3-6 have been prepared and reacted with n-Bu3SnH to generate the corresponding radicals for examination of the cyclization reactions of these reactive intermediates.The observed hydrocarbon products indicate that cyclization occurs for the n=3,4, and 5 radicals but not for the n=6 species.The n=3 radical isomerizes very efficiently by intramolecular addition to the sp carbon of the allene group.The n=5 intermediate reacts relatively slowly by attack at the near sp2 carbon.Both cyclization modes are observed for the n=4 species.The details of these radical cyclizations are discussed.
