A Chemical, Spectroscopic, and Theoretical Assessment of the Lewis Acidity of LiClO4 in Diethyl Ether

Richard M. Pagni, George Kabalka, Satinder Bains, Miechelle Plesco, Jennifer Wilson, John Bartmess

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

Moderate diastereoselectivity is observed in the reaction of cyclopentadiene with dimethyl maleate and optically active dimenthyl fumarate in LiClO4/diethyl ether. Moderate regioselectivity is also seen in the reaction of isoprene and methyl acrylate in the same medium. NMR experiments and MNDO calculations, in conjunction with published work on Li+ in the gas phase, demonstrate that the strong, intrinsic Lewis acidity of Li+ is moderated in ether by complexation to the solvent and the counterion.

Original languageEnglish (US)
Pages (from-to)3130-3133
Number of pages4
JournalJournal of Organic Chemistry
Volume58
Issue number11
DOIs
StatePublished - Jan 1 1993
Externally publishedYes

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Acidity
Ether
Cyclopentanes
Regioselectivity
Fumarates
Complexation
Gases
Nuclear magnetic resonance
Experiments
lithium perchlorate
methyl acrylate
isoprene
dimethyl maleate

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

A Chemical, Spectroscopic, and Theoretical Assessment of the Lewis Acidity of LiClO4 in Diethyl Ether. / Pagni, Richard M.; Kabalka, George; Bains, Satinder; Plesco, Miechelle; Wilson, Jennifer; Bartmess, John.

In: Journal of Organic Chemistry, Vol. 58, No. 11, 01.01.1993, p. 3130-3133.

Research output: Contribution to journalArticle

Pagni, Richard M. ; Kabalka, George ; Bains, Satinder ; Plesco, Miechelle ; Wilson, Jennifer ; Bartmess, John. / A Chemical, Spectroscopic, and Theoretical Assessment of the Lewis Acidity of LiClO4 in Diethyl Ether. In: Journal of Organic Chemistry. 1993 ; Vol. 58, No. 11. pp. 3130-3133.
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