原创力文档Investigation into the Regiochemistry of 1,3-Dipolar Cycloaddition of C,N-Diphenyl Nitrone with Some Vinyl Sulfoximines as Dipolarophile： Theoretical Studies.pdfVIP
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Investigation into the Regiochemistry of 1,3-Dipolar Cycloaddition of C,N-Diphenyl Nitrone with Some Vinyl Sulfoximines as Dipolarophile： Theoretical Studies.pdf
FULLPAPER
InvestigationintotheRegiochemistryof1，3-Dipolar
CycloadditionofC，N-DiphenylNitronewithSome
VinylSulfoximinesasDipoIarOph-Ie：TheoreticalStudies
Moeinpour，Farid
DepartmentofChemistry，FacultyofSciences，IslamicAzadUniversity，BandarAbbasBranch，
BandarAbbas7915893144，lran
Theregiochemistryof1，3一dipolarcycloaddition reactionsofC，N-diphenylnitronewith somevinylsulofx—
iminesasdipolarophilewasinvestigatedusingdensityfunctionaltheory(DFT)一basedreactivityindexesandactiva—
tionenergycalculationsatB3LYP／6—31G(d)levelofhteory．Analysisofthegeome~esandbondorders(BOs)at
theTSstructuresassociatedwiht thedifferentreactionpathwaysshowshtathtese1．3-dipolra cycloadditionreac。
tionsoccurviaanasynchronousconcertedmechanism．Analysisofhtelocalelectrophilicityandnuc1eophmcitvin．
dexespermitsaninterpretationabouttheregioselectivityofthese1，3-dipolra cycloadditionreactions．Thetheoreti
calresultsobtalned in thework cleralypredicthteregiochemistry ofhteisolated cycloadductsandagree to
experimentaloutcomes．
Keywords regioselectivity，cycloaddition，densityfunctionalcalculations
Introduction literature． The 1I3一DC reactionsofnitroneswithal—
Kenesrae an lmoortantmetlaod torprepra ln~ lsoxazoll—
Thecycloadditionof1,3一dipolarspeciestoanalkene
dines in a reglOSeleCt1ve and stereoselective mna ner．
forthesynhtesisoffive—memberedringsisaclassicand
IsOxazO1idineshavebee
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