Molecular orbital study of the cycloaddition reactions of cyclopentyne lumomer

AM1 molecular orbital calculations of the reaction path for [2+2] and [2+4] cycloaddition of cyclopentyne lumomer ( 2) with ethylene and 1,3-butadiene show concert for the former process and stepwise character for the latter. The result are consistent with Dewar's theory of orbital isomerism in...

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Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 4; pp. 603 - 606
Main Authors Gilbert, John C., Kirschner, Steven
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 1993
Subjects
cycloaddition
Cyclobutylidenylcarbene
cyclopentyne
lumomer
orbital crossing
lumomer
cycloaddition
orbital crossing
Cyclobutylidenylcarbene
cyclopentyne
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Summary:AM1 molecular orbital calculations of the reaction path for [2+2] and [2+4] cycloaddition of cyclopentyne lumomer ( 2) with ethylene and 1,3-butadiene show concert for the former process and stepwise character for the latter. The result are consistent with Dewar's theory of orbital isomerism in pericyclic reactions. AM1 molecular orbital calculations of the reaction path for [2+2] and [2+4] cycloaddition reactions of cyclopentyne lumomer, 2, with ethylene and 1,3-butadiene show concert for the former process and stepwise character for the latter. The results are consistent with Dewar's theory of orbital isomerism in pericyclic reactions.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)61630-1