Nucleophilic aromatic substitution on (o-methoxyaryl) oxazolines. A convenient synthesis of o-alkyl-, o-alkenyl-, and o-arylbenzoic acids

AI Meyers, R Gabel, ED Mihelich

Index: Meyers,A.I. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 1372 - 1379

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Citation Number: 175

Abstract

Reaction of o-(methoxy) aryloxazolines 1 with organolithium or Grignard reagents results in methoxy displacement to the ()-(alkyl)-, o-(aryl)-, and o-(viny1) aryloxazolines 3. A variety of organometallics were employed and only those considered to be delocalized anions failed to displace the methoxy group. Various poly (methoxy) aryloxazol-ines I la-e) were investigated, and the reactions proceeded with general success, the yields dropping off in ...