1995
DOI: 10.1021/ar00050a004
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Pericyclic Reaction Transition States: Passions and Punctilios, 1935-1995

Abstract: Pericyclic reactions may be the most important class of organic reactions. Certainly, the mechanisms of these reactions have been the subject of the most heated and interesting controversies. Woodward and Hoffmann defined the concept of a pericyclic reaction: a concerted reaction in which all bonds are made or broken around a circle. Although the Woodward-Hoffmann rules declare what may and may not happen, the rules served not to settle mechanistic questions but to raise the stakes on what were already lively … Show more

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Cited by 663 publications
(420 citation statements)
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“…After several decades of debate [18], it is quite clear that the classic pericyclic reactions with six electrons involved in bonding changes-Diels-Alder, Cope, six electron electrocyclic reactions, and 1,5-sigmatropic shifts, indeed have aromatic transition states as judged by geometries [19] and magnetic properties [20]. The energies of these pericyclic reactions are also relatively favorable as compared to forbidden (antiaromatic) pericyclic processes.…”
Section: Methodsmentioning
confidence: 99%
“…After several decades of debate [18], it is quite clear that the classic pericyclic reactions with six electrons involved in bonding changes-Diels-Alder, Cope, six electron electrocyclic reactions, and 1,5-sigmatropic shifts, indeed have aromatic transition states as judged by geometries [19] and magnetic properties [20]. The energies of these pericyclic reactions are also relatively favorable as compared to forbidden (antiaromatic) pericyclic processes.…”
Section: Methodsmentioning
confidence: 99%
“…Two pathways are conceivable 95 . (1) The reaction pathway happens in two incoherent intermediate steps-the reactants are hinged together, then tethered to complete the cyclization.…”
Section: Function From Coherencementioning
confidence: 99%
“…The cycloaddition reactions of the nitrile oxides 1 with the cyanoenamines 2 proved to be highly regioselective, leading to a single regioisomer. The regioselectivity of the cycloaddition reactions of nitrile oxides with dipolarophiles and their mechanism have been explained in the literature [17]. As in the case of the cycloaddition reactions of arylazides [16], the α-cyanoenamines 2 behave as the synthetic equivalents of the corresponding aminoacetylenes [18].…”
Section: Resultsmentioning
confidence: 99%