Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Formation of 1,2-Dioxanes by the Use of Tris(2,4-pentanedionato)manganese(III) or Manganese(III) Acetate
Hiroshi NishinoShin-ichi TategamiTakashi YamadaJames D. KorpKazu Kurosawa
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1991 Volume 64 Issue 6 Pages 1800-1809

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Abstract

The reactions of 1,1-diphenylethene, 1,1-bis(4-chlorophenyl)ethene, 1,1-bis(4-methoxyphenyl)ethene, 1,1-bis(4-methylphenyl)ethene, 1,1-bis(4-fluorophenyl)ethene, styrene, 1-octene, cyclohexene, and cyclooctene with tris(2,4-pentanedionato)manganese(III) ([Mn(acac)3]) in acetic acid at room temperature give 4-acetyl-3-methyl-1,2-dioxan-3-ol in 8–92% yields, together with 3-acetyl-4-hydroxy-3-hexene-2,5-dione. The similar reactions of 1,1-diphenylethene with 2,4-pentanedione, 3-methyl-2,4-pentanedione, 3-ethyl-2,4-pentanedione, 1-phenyl-1,3-butanedione, acetoacetanilide, and 1,3-cyclohexanedione in the presence of manganese(III) acetate also give the corresponding cyclic peroxide in good to moderate yields. The mechanisms of manganese(III)-induced 1,2-dioxane ring formation and concomitant radical side reaction are discussed.

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