TY - JOUR
T1 - 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
AU - Mori, Mitsuyuki
AU - Sugiyama, Tomohito
AU - Nojima, Masatomo
AU - Kusabayashi, Shigekazu
AU - McCullough, Kevin J.
PY - 1992
Y1 - 1992
N2 - 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)-a-(4-methylphenyl)-a-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. © 1992 American Chemical Society.
AB - 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)-a-(4-methylphenyl)-a-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. © 1992 American Chemical Society.
UR - http://www.scopus.com/inward/record.url?scp=0012730823&partnerID=8YFLogxK
M3 - Article
SN - 0022-3263
VL - 57
SP - 2285
EP - 2294
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 8
ER -