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
URL:
http://dx.doi.org/10.1002/poc.610071109
