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  • 1
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Transition states for the hetero-Diels-Alder addition of formaldehyde, formaldimine, diazene and nitrosyl hydride to cyclopentadiene were located with ab initio molecular orbital calculations. Asynchronous transition structures were located for the asymmetric hetero-dienophiles, whereas the symmetrical hetero-dienophile, cis-diazene, produced a synchronous transition structure. The relative reactivities are in good agreement with the LUMO energies of the hetero-dienophiles, and the transition states with the exo oxygen or nitrogen lone pairs have lower energies than the corresponding endo lone electron pair transition states. Endo/exo energy differences are much higher than in the addition of ethylene derivatives to cyclopentadiene.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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