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Applications of Phase Transfer Catalysis to Arenediazonium Cation Chemistry
Author(s) -
Gokel George W.,
Ahern Michael F.,
Beadle James R.,
Blum Lorna,
Korzeniowski Stephen H.,
Leopold Ahuva,
Rosenberg David E.
Publication year - 1985
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198500106
Subject(s) - chemistry , yield (engineering) , diazo , catalysis , reagent , phase transfer catalyst , halogenation , diazonium compounds , cycloaddition , pyridazine , phase (matter) , combinatorial chemistry , potassium , organic chemistry , photochemistry , materials science , metallurgy
Abstract Arenediazonium cations have been known for many years but the synthetic utility has been diminished by their lack of stability and by their proclivity for undergoing sundry side reactions. Arenediazonium BF 4 and PF 6 salts are generally stable solids, but are relatively insoluble in nonpolar organic media. Crown complexation and other forms of phase transfer catalysis increase solubility and allow numerous synthetic transformations to be conducted in good yield. The yield improvements result from a reduction in competing side reactions rather than any fundamental change in mechanism. The reactions to which the phase transfer technique is successfully applied are diazo coupling, reduction, halogenation, arylation and cyclization. In the latter case, the use of potassium superoxide is sometimes a more efficacious reagent than potassium acetate. The phase transfer approach can be used in the high yield synthesis of arenediazosulfones and arenediazocyanides. The latter undergo cycloaddition with many dienes to yield pyridazine derivatives.