The Journal of organic chemistry

Probing Persistent Intramolecular C− H··· X (X= O, S, Br, Cl, and F) Bonding in Solution Using Benzyl Meldrum's Acid Derivatives

E Fillion, A Wilsily, D Fishlock

Index: Fillion, Eric; Wilsily, Ashraf; Fishlock, Dan Journal of Organic Chemistry, 2009 , vol. 74, # 3 p. 1259 - 1267

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Citation Number: 20

Abstract

Persistent intramolecular interactions between acidic C− H hydrogens and a variety of acceptors (X)(X= O, S, Br, Cl, and F) in solution were probed by 1H NMR experiments, using 5-benzyl Meldrum's acid derivatives. To bring about formation of intramolecular C− H··· X bonding, ortho-substituted benzyl Meldrum's acids were designed, for which hydrogen bonding occurred through a six-membered ring. Introduction of substituents on the ...

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