The Journal of Organic Chemistry

Deconjugative alkylation of. alpha.,. beta.-acetylenic esters by electrogenerated base

M Tokuda, O Nishio

Index: Tokuda, Masao; Nishio, Osamu Journal of Organic Chemistry, 1985 , vol. 50, # 10 p. 1592 - 1596

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Citation Number: 10

Abstract

Electrolysis of ethyl propiolate (1) and an excew of methyl iodide at a platinum cathode in hexamethylphosphoric triamide (HMPA) or Nfl-dimethylformamide (DMF) solution containing tetra-n-butylammonium salt gave the acetylenic esters 2, 3, and 4. Similar electrochemical reactions of a,@-acetylenic esters 2, 5, and 9 with methyl iodide took place in good yields to give the corresponding a, a-dimethyl@, y-acetylenic esters 3 and 4, 4, and 10, ...