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1,3‐Dipolar Cycloaddition of 4‐Chlorobenzonitrile Oxide with Some Dipolarophiles: Theoretical Analysis of Regioselectivity
Author(s) -
Bakavoli Mehdi,
Moeinpour Farid,
SardashtiBirjandi Arezoo,
Davoodnia Abolghasem
Publication year - 2013
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.822
Subject(s) - chemistry , regioselectivity , nitrile , cycloaddition , reactivity (psychology) , density functional theory , computational chemistry , oxide , 1,3 dipolar cycloaddition , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Reaction of 4‐chlorobenzonitrile oxide ( 2 ) which was generated in situ with acrylo nitrile ( 3 ), vinyl acetate ( 4 ) and allyl bromide ( 5 ) as dipolarphile afforded the new cycloadducts 6a , 7a , and 8a compounds, respectively. Reactivity and regiochemistry of these reactions were investigated using activation energy calculations and density functional theory‐based reactivity indexes. The theoretical 13 C NMR chemical shifts of the cycloadducts which were obtained by gauge‐invariant atomic orbital method were comparable with the observed values.