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Green organic syntheses: Organic carbonates as methylating agents
Author(s) -
Tundo Pietro,
Perosa Alvise
Publication year - 2002
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.10007
Subject(s) - reagent , chemistry , nucleophile , reactivity (psychology) , catalysis , selectivity , halide , organic base , organic chemistry , combinatorial chemistry , methylation , medicine , biochemistry , alternative medicine , pathology , gene
Dimethylcarbonate (DMC) is a valuable methylating reagent that can replace methyl halides and dimethylsulfate in the methylation of a variety of nucleophiles. It couples tunable reactivity and unprecedented selectivity towards mono‐ C‐ and mono‐ N‐ methylation. In addition, it is a prototype example of a green reagent , because it is nontoxic, is made by a clean process, is biodegradable, and reacts in the presence of a catalytic amount of base, thereby avoiding the formation of undesirable inorganic salts as by‐products. Depending on the reaction conditions, DMC can be reacted under plug‐flow, CSTR, or batch conditions. Other remarkable reactions are those where DMC behaves as an oxidant. The reactivity of other carbonates is reported as well. © 2002 The Japan Chemical Journal Forum and John Wiley & Sons, Inc. Chem Rec 2: 13–23, 2002