A three-center orbital interaction in the Diels-Alder reactions catalyzed by Lewis acids

Journal of Organic Chemistry

Volumn 65, Issue 6, 2000, Pages 1830-1841

  Yamabe, Shinichi ^a   Minato, Tsutomu ^b  

^a NARA UNIVERSITY OF EDUCATION   (Japan)

^b NARA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; ACROLEIN; ALUMINUM CHLORIDE; METAL COMPLEX; TIN CHLORIDE; ZINC CHLORIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; GEOMETRY; REACTION ANALYSIS;

EID: 0034708425     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9919310     Document Type: Article

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46. (a) There is a complete trans addition path with TS (1) leading to an alternative zwitterionic intermediate (2). The activation energy of 1 is even smaller (1.0 kcal/mol by B3LYP/6-311+G(2d,p) SCRF// B3LYP/6-31G* SCRF) than that of [4 + 2] TS. But, the resultant intermediate, 2, does not have a channel to any ring closures, and 2 is merely under an equilibrium of association and dissociation. (equation presented) zwitterionic intermediate (2)
47. 3 (AC-LA), total energies of TSs calculated by RHF/3-21G//RHF/ 3-21G method are -2034.173987 au ([4 + 2] addition) and -2034.170203 au (one-center addition). For a reaction between 2-aminobutadiene and AC-LA, they are -2011.276254 au ([4 + 2] addition) and -2011.269103 au (one-center addition).
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