1990
DOI: 10.1016/0166-1280(90)85073-v
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The vinylcyclopropane rearrangement: An AM1 study

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Cited by 14 publications
(7 citation statements)
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“…The relative order also follows the polarizability of the substituents. Related calculations on hydroxy- and cyano-substituted vinylcyclopropanes have been reported. , …”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The relative order also follows the polarizability of the substituents. Related calculations on hydroxy- and cyano-substituted vinylcyclopropanes have been reported. , …”
Section: Resultsmentioning
confidence: 99%
“…Related calculations on hydroxy-and cyano-substituted vinylcyclopropanes have been reported. 44,45 Woodward-Hoffmann allowed si stereochemistry are observed. As shown in Figure 12, as the cyclopropane bond stretches, an anti-aromatic interaction develops involving the breaking bond orbital and the occupied π orbital.…”
Section: Scheme 2 Types Of Transition Structuresmentioning
confidence: 99%
“…Further, the four transition structures in the four cases could well be isometric, deuterium-labeled versions of w x the transition structure for the 1,3 carbon shift as defined geometrically through theoretical work by Quirante, Enrıguez, and Hernando, 94,95 and bý Houk and co-workers 96 :…”
Section: Hypothetical Mechanismmentioning
confidence: 99%
“…The calculated activation energy for the isomerization was 63.6-63.8 kcal/mol. 82,83 In the 1990s the challenge to computational chemistry posed by the vinylcyclopropane rearrangement, and by other [1,3] carbon sigmatropic shifts, continued to attract persistent attention. In a 1992 review on hydrocarbon pericyclic reactions, the vinylcyclopropane rearrangement was still considered to be geometrically constrained to be suprafacial on the allyl system, while having an option of either retention or inversion at the migrating carbon.…”
Section: Computational Studies Of the Rearrangementmentioning
confidence: 99%