The Journal of Organic Chemistry

Nonbenzenoid aromatic systems. XI. Synthesis and buffered acetolysis of 2-(2-azulyl) ethyl tosylate and nosylate

RN McDonald, JM Richmond

Index: McDonald,R.N.; Richmond,J.M. Journal of Organic Chemistry, 1975 , vol. 40, p. 1689 - 1694

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Citation Number: 21

Abstract

The synthesis of 2-(2-azulyl) ethanol (1-OH) was accomplished starting with methyl or ethyl 2-chloro-1-azulenecarboxylate (6) and involved nucleophilic substitution at Cz with sodium methylcyanoacetate followed by lithium iodide ester halogenodealkylation with concomitant bisdecarboxylation to 2-azulylacetonitrile (10). Hydrolysis of 10 followed by diborane reduction of the acetic acid 11 gave 1-OH. The kinetics of buffered acetolysis of 1-OTs and ...