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Mechanism of cycloaddition to indolizines
Author(s) -
Simonyan Vahan V.,
Zinin Alexander I.,
Babaev Eugene V.,
Jug Karl
Publication year - 1998
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199803)11:3<201::aid-poc980>3.0.co;2-w
Subject(s) - cycloaddition , chemistry , indolizine , ring (chemistry) , computational chemistry , nucleophile , pericyclic reaction , electrophile , reaction mechanism , 1,3 dipolar cycloaddition , transition state , photochemistry , medicinal chemistry , organic chemistry , catalysis
The peculiarities of [8+2] cycloaddition reactions of indolizines with dienophiles are reviewed. Quantum chemical SINDO1, AM1 and ab initio calculations of transition states were performed for [8+2] cycloaddition reactions of indolizine and 6‐nitroindolizine with a series of alkenes with donor and acceptor groups. The calculations predict a dipolar cycloaddition mechanism (electrophilic addition and ring closure) for reactions of indolizine and 6‐nitroindolizine with nitroethylene. For the reaction of 6‐nitroindolizine with N , N ‐dimethylaminoethylene, the predicted mechanism corresponds to a previously unknown ‘inverse’ dipolar cycloaddition (nucleophilic addition and ring closure). © 1998 John Wiley & Sons, Ltd.