Synthesis and x-ray analysis of dihydro-1, 2, 4, 5-trioxazine. Evidence of a stepwise mechanism for the [3+ 3] cycloaddition of carbonyl oxides with nitrones
…, T Sugiyama, M Nojima, S Kusabayashi…
Index: Mori, Mitsuyuki; Sugiyama, Tomohito; Nojima, Masatomo; Kusabayashi, Shigekazu; McCullough, Kevin J. Journal of Organic Chemistry, 1992 , vol. 57, # 8 p. 2285 - 2294
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Citation Number: 15
Abstract
Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo [3+ 31 cycloaddition reactions with nitrones affording dihydro-1, 2, 4, 5-trioxazines in fair to excellent, yield. The structures of dihydro-3, 5, 6-tri-phenyl-l, 2, 4, 5-trioxazine (5f) and dihydro-3-cyclohexyl-5- methyl-6, 6-dipheny1-1, 2, 4, 5-trioxazine (5t) were un-ambiguously determined by X-ray analysis. Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)-or (Z)- ...
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