Journal of the American Chemical Society

Macro Rings. XXVI.[2.2] Paracyclophanyl as a Neighboring Group

DJ Cram, LA Singer

Index: Cram,D.J.; Singer,L.A. Journal of the American Chemical Society, 1963 , vol. 85, p. 1075 - 1079

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Citation Number: 19

Abstract

The ability of [2.2] paracyclophane to act as a neighboring group when attached to C, or Cp of a carbonium ion-forming system has been determined through reactivity comparisons of I, 11, I11 and IV. Solvolysis rate measurements and activation parameters demonstrated that the (2.2 lparacyclophanyl system is a better neighboring group in solvolytic reactions than its open-chain counterpart. Hydrolysis of optically pure bromide I in 80% dioxane20% water ...