Reactivity of long conjugated systems: Selectivity of Diels-Alder cycloaddition in oligofurans

Organic Letters

Volumn 14, Issue 2, 2012, Pages 502-505

  Gidron, Ori ^a   Shimon, Linda J W ^a   Leitus, Gregory ^a   Bendikov, Michael ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84856082864     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202987e     Document Type: Article

References (35)

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32. All calculations were performed using Gaussian 09 software. Frisch, M. J.; Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009. See Supporting Information for full reference.
33. The B3LYP/6-31G(d) level was chosen since it is known to be a reliable method for studying DA reactions (see Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036), although this method is also known to overestimate the activation barriers of a DA reaction by a few kcal/mol, which is in agreement with our benchmark calculations
34. The M06-2X/6-31G(d) level was chosen since it is known to reproduce dispersion interaction in organic systems correctly, which is important for studying the transition state of DA reactions (see Zhao, Y.; Truhlar, D. Acc. Chem. Res. 2008, 41, 157)
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