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Computational investigation of the suitability of heterocyclic aromatic compounds with two heteroatoms in the 1 and 3 ring positions as dienes for the diels alder reaction
Author(s) -
Jursic Branko S.
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350642
Subject(s) - chemistry , cycloaddition , reactivity (psychology) , heteroatom , cyclopropene , computational chemistry , furan , ring (chemistry) , diels–alder reaction , regioselectivity , transition state , density functional theory , acetylene , organic chemistry , medicinal chemistry , catalysis , medicine , alternative medicine , pathology
Semiempirical and density functional theory computational studies were carried out with the target determining the reactivity of five membered heterocycles with heteroatoms in the 1 and 3 positions as dienes for Diels‐Alder reactions. The relative reactivity was evaluated in their reaction with acetylene, ethylene, and cyclopropene as dienophiles for cycloaddition. Qualitative criteria such as uniformity of heterocycle bond orders, change of bond orders and frontier molecular orbital energies in transformation of reactants into transition state structures were used to determine the relative reactivity in comparison with furan. These results are compared with the computed activation barriers as well as with experimental findings, where available. If cycloaddition is feasible with these heterocycles, a new synthetic transformation of simple organic compounds to valuable prostaglandin derivatives can be accomplished.