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Volumn , Issue 5, 2009, Pages 721-729

Is the elimination of lithium alkoxide easier from a vinyllithium or from an alkyllithium? A DFT study of the aromatization of 3-vinylidene-2,3- dihydrobenzofurans to benzofurans

Author keywords

Acetals; Aromatization; Density functional calculations; Elimination; Lithium; Reaction mechanism

Indexed keywords


EID: 60849090741     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800828     Document Type: Article
Times cited : (7)

References (35)
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    • anti isomers, resulting from the isomerization of the original syn product, were observed when the resulting vinyllithium was stabilized, see: a W. Bauer, M. Feigel, G. Müller, P. v. R. Schle-yer, J. Am. Chem. Soc. 1988, 110, 6033-6046;
    • anti isomers, resulting from the isomerization of the original syn product, were observed when the resulting vinyllithium was stabilized, see: a) W. Bauer, M. Feigel, G. Müller, P. v. R. Schle-yer, J. Am. Chem. Soc. 1988, 110, 6033-6046;
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    • For examples of transition states for the protonation of organolithium derivatives, see: a M. L. McKee, J. Am. Chem. Soc. 1987, 109, 559-565;
    • For examples of transition states for the protonation of organolithium derivatives, see: a) M. L. McKee, J. Am. Chem. Soc. 1987, 109, 559-565;
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    • Note that the ideal trajectory for the protonation of an sp2 carbanion does not seem to be known
    • 2 carbanion does not seem to be known.
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    • To keep this paper focused on the key points, we did not examine the deprotonation of 3A into 3ALi. Therefore, the energy barrier associated with this step is not known and could play a role in the overall kinetics of the reaction.
    • To keep this paper focused on the key points, we did not examine the deprotonation of 3A into 3ALi. Therefore, the energy barrier associated with this step is not known and could play a role in the overall kinetics of the reaction.
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    • see for instance: e
    • see for instance: e) D. B. Chesnut, J. Phys. Chem. A 2000, 104, 7635-7638;
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.