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Volumn 87, Issue 6, 2009, Pages 760-774

Novel formation of isoxazoline N-oxide in addition to Michael adduct from the reaction of ß-nitrostyrenes with 2-methoxyfuran-Experimental and theoretical studies

Author keywords

Density functional calculations; Nitrogen heterocycles; Reaction mechanisms; Rearrangement; Zwitterions

Indexed keywords

DENSITY FUNCTIONAL CALCULATIONS; NITROGEN HETEROCYCLES; REACTION MECHANISMS; REARRANGEMENT; ZWITTERIONS;

EID: 67650340987     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V09-068     Document Type: Article
Times cited : (9)

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    • The yields were calculated from the products isolated after column chromatography. For the isoxazoline, the separation was difficult; therefore, a small percentage loss may result.
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    • Mulliken and natural population analysis atomic charge indicate that the C1 center has the largest degree of electrophilic activation. Thus, the most favorable interaction takes place between the C1 and C6 atoms with the formation of the (4+2) cycloadduct, which is at odds with the experimental results. Thus, these rearrangement reactions cannot be successfully analyzed using these population analysis methods.
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    • 2 group has the higher electrophilic activity, but the length from the nucleophilic center C4 is over 4.5 A° , so the O3-atom should not take part in bond formation.
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