The regiospecific phase transfer catalyzed reductive carbonylation of azadienes
Author(s) -
Howard Alper,
Shiyamalie Amaratunga
Publication year - 1983
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v83-232
Subject(s) - chemistry , carbonylation , catalysis , carbon monoxide , allylic rearrangement , benzene , methyl iodide , iodide , chloride , cobalt , photochemistry , medicinal chemistry , organic chemistry
Reaction of an azadiene with cobalt carbonyl, carbon monoxide, and methyl iodide under phase transfer catalysis conditions (benzene, water or aqueous NaOH, benzyltriethylammonium chloride) affords allylic amides in reasonable yields. This regiospecific reaction is sensitive to the concentration of base. One can also effect this transformation using acidic catalysis. A mechanism is proposed for the reductive carbonylation reaction.
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