Canadian Journal of Chemistry

The synthesis of norbornanes with functionalized carbon substituents at a bridgehead. 1-(3-Oxonorborn-1-yl) ethanone and 1-(3-oxonorborn-1-yl)-2-propanone

P Yates, M Kaldas

Index: Yates, Peter; Kaldas, Magdy Canadian Journal of Chemistry, 1992 , vol. 70, # 5 p. 1492 - 1505

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Citation Number: 4

Abstract

Treatment of 2-norobornene-1-carboxylic acid (7) with one equivalent of methyllithium in ether followed by a second molar equivalent after dilution with tetrahydrofuran gave 1- (norborn-2-en-lyl) ethanone (10) and only a trace of the tertiary alcohol 11. Reaction of 7 with formic acid followed by hydrolysis gave a 4: 3 mixture of exo-3-and exo-2- hydroxynorbornane-1-carboxylic acid (16 and 17), whereas oxymercuration- ...