Regiochemistry in alkylation, acylation and methoxycarbonylation of alkali salts from 2-substituted alkenylpropanedinitriles

H Karlsen, PH Songe, LK Sunsby, LC Hagen…

Index: Karlsen, Hege; Songe, Pal H.; Sunsby, Lise Kristin; Hagen, Lise Cathrine; Kolsaker, Per; Romming, Christian Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 5 p. 497 - 507

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Citation Number: 12

Abstract

Alkali salts (4−) of several 2-substituted alkenylpropanedinitriles are prepared, isolated and characterised by 1 H and 13 C NMR spectroscopy. By treating the salt 4a− with 4a a dimer, 2- dicyanomethylene-6-methyl-4, 6-diphenyl-1, 2, 5, 6-tetrahydronicotinonitrile 6, is formed, for which a single-crystal X-ray structure is presented. Alkylation of the ambident salts 4− with MeX (X= I, Tf, or Br) leads to regioisomers, 1-and 3-alkylation, and comparison with O vs. ...