Electroorganic chemistry. 46. A new carbon-carbon bond forming reaction at the. alpha.-position of amines utilizing anodic oxidation as a key step

T Shono, Y Matsumura, K Tsubata

Index: Shono, Tatsuya; Matsumura, Yoshihiro; Tsubata, Kenji Journal of the American Chemical Society, 1981 , vol. 103, # 5 p. 1172 - 1176

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Citation Number: 250

Abstract

Abstract: A new carbon-carbon bond forming reaction at the a-position of primary and secondary amines has been exploited. The method involves anodic oxidation of urethanes derived from the primary and secondary amines and subsequent acid-catalyzed reaction of the resulting a-methoxylated urethanes with nucleophiles such as electron-rich olefins and active methylene compounds. The intermediary participation of (carbometh0xy) iminium ...