Journal of Organic Chemistry p. 2285 - 2294 (1992)
Update date:2022-08-04
Topics:
Mori, Mitsuyuki
Sugiyama, Tomohito
Nojima, Masatomo
Kusabayashi, Shigekazu
McCullough, Kevin J.
Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo <3 + 3> cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield.The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis.Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-α-(4-methylphenyl)-α-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts.This result, in conjunction with the structure of the relevant 5t, suggests that the <3 + 3> cycloaddition proceeds by a stepwise mechanism.
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