A computational examination of Diels-Alder reactions with 1,3- cyclopentadienes bearing anionic and cationic substituents at C-5

Tetrahedron Letters

Volumn 41, Issue 7, 2000, Pages 995-998

  Xidos, James D ^a   Poirier, Raymond A ^a   Burnell, D Jean ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

Cyclopentadienes; Diels Alder reactions; Electronic effects; Steric and strain effects

Indexed keywords

ANION; CATION; CYCLOPENTADIENE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; MATHEMATICAL ANALYSIS; PREDICTION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034639733     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02225-X     Document Type: Article

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17. Analytical force constants were evaluated to ensure that ground state molecules had no imaginary frequencies and that transition states were first-order saddle-points.
18. A transition state for the anti-addition of protonated 2 could not be found at the HF/6-31++G(d)//HF/6-31++G(d) level; dissociation of the C-O bond is predicted instead. However, an hypothetical anti-transition state was approximated by fixing the C-O bond to a length consistent with that seen in other anti-transition states.