Reactions of Enol Ethers with Carbenes. V. Rearrangements of Dihalocyclopropanes Derived from Six-, Seven-, and Eight-Membered Cyclic Enol Ethers1

WE Parham, RW Soeder…

Index: Parham,W.E. et al. Journal of the American Chemical Society, 1965 ,  vol. 87,  # 2  p. 321 - 328            

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Citation Number: 22

Abstract

1, I-Dihalocyclopropanes have been prepared from enol ethers derived from cyclohexanone, cycloheptanone, and cyclooctanone. The product derived from cyclohexanone afjords I-ethoxy-1, 3, 5-cycloheptatriene (5) in 55% over-all yield by a two- step process involving pyridine with subsequent reaction of the intermediate chlorodiene 4 with potassium t-butoxide, or in 37z yield by a onestep-process involving quinoline. ...