Nucleophilic substitution reactions of sulfur-substituted cyclohexanone acetals: An analysis of the factors controlling stereoselectivity

Susan B. Billings, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

The reactions of cyclohexanone acetals substituted with thiophenyl groups (and other heteroatoms) at C-2 demonstrate the powerful influence that these substituents have on the stereoselectivity of nucleophilic substitution reactions. The trans selectivities of these reactions correlate with the behavior of the corresponding ketones. These experiments lend support to the possibility that the reactions of the acetals, which proceed via oxocarbenium ions, are operating under Felkin-Anh control.

Original languageEnglish (US)
Pages (from-to)5171-5178
Number of pages8
JournalJournal of Organic Chemistry
Volume71
Issue number14
DOIs
StatePublished - Jul 7 2006

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Stereoselectivity
Acetals
Sulfur
Substitution reactions
Ketones
Ions
Experiments
cyclohexanone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Nucleophilic substitution reactions of sulfur-substituted cyclohexanone acetals : An analysis of the factors controlling stereoselectivity. / Billings, Susan B.; Woerpel, Keith.

In: Journal of Organic Chemistry, Vol. 71, No. 14, 07.07.2006, p. 5171-5178.

Research output: Contribution to journalArticle

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