Rapid nucleophilic substitutions on cyclopentadienyl iodide and bromide

R Breslow, JW Canary

Index: Breslow, Ronald; Canary, James W. Journal of the American Chemical Society, 1991 , vol. 113, # 10 p. 3950 - 3951

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Citation Number: 20

Abstract

Abstract: Cyclopentadienyl iodide reacts with tetrabutylammonium bromide to afford cyclopentadienyl bromide ca. 10 times as rapidly as cyclopentyl iodide reacts under the same conditions. Cyclopentadienyl bromide reacts with tetrabutylammonium iodide ca. Id times as rapidly as does cyclopentyl bromide. To check for allylic substitution, 5- icdocyclopentadiene was metallated with potassium hexamethyldisilazide, and the ...