TY - JOUR A1 - Golub, Tatiana A1 - Becker, James Y. T1 - Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis JF - Beilstein Journal of Organic Chemistry PY - 2018/// VL - 14 SP - 861 EP - 868 SN - 1860-5397 DO - 10.3762/bjoc.14.72 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.14.72 KW - anodic oxidation KW - bisamides KW - constant current electrolysis KW - methoxylation N2 - In general, bisamides derived from diamines and involving 3 and 4 methylene groups as spacers between the two amide functionalities behave similar to monoamides upon anodic oxidation in methanol/LiClO4 because both types undergo majorly mono- and dimethoxylations at the α-position to the N atom. However, in cases where the spacer contains two methylene groups only the anodic process leads mostly to CH2–CH2 bond cleavage to afford products of type RCONHCH2OCH3. Moreover, upon replacing LiClO4 with Et4NBF4 an additional fragmentation type of product was generated from the latter amides, namely RCONHCHO. Also, the anodic process was found to be more efficient with C felt as the anode, and in a mixture of 1:1 methanol/acetonitrile co-solvents. ER -