The Journal of Organic Chemistry

Intramolecular nucleophilic acyl substitution reactions of halo-substituted esters and lactones. New applications of organosamarium reagents

GA Molander, JA McKie

Index: Molander, Gary A.; McKie, Jeffrey A. Journal of Organic Chemistry, 1993 , vol. 58, # 25 p. 7216 - 7227

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Citation Number: 106

Abstract

Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium (I1) iodide as the reductive coupling agent. Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the ...