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Dimethyl Carbonate as an Ambident Electrophile
Open accessAbstract
[reaction: see text] The features of various anions having different soft/hard character (aliphatic and aromatic amines, alcohoxydes, phenoxides, thiolates) are compared with regard to nucleophilic substitutions on dimethyl carbonate (DMC), using different reaction conditions. Results are well in agreement with the Hard-Soft Acid-Base (HSAB) theory. Accordingly, the high selectivity of monomethylation of CH(2) acidic compounds and primary aromatic amines with DMC can be explained by two different subsequent reactions, which are due to the double electrophilic character of DMC. The first step consists of a hard-hard reaction and selectively produces a soft anion, which, in the second phase, selectively transforms into the final monomethylated product, via a soft-soft nucleophilic displacement (yield >99% at complete conversion, using DMC as solvent).
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Cites
Pearson, R. G. (1963) · Journal of the American Chemical Society · doi:10.1021/ja00905a001 · Cited by 10,475
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The reactions of dimethyl carbonate and its derivatives
Tundo, P., Musolino, M., & Aricò, F. (2018) · Green Chemistry · doi:10.1039/c7gc01764b · Cited by 264
Self-citationTBD catalysis with dimethyl carbonate: a fruitful and sustainable alliance
Mutlu, H., Ruiz, J., Solleder, S. C., & Meier, M. A. R. (2012) · Green Chemistry · doi:10.1039/c2gc35191a · Cited by 116
Metadata
- Authors
- Tundo, P., Rossi, L., & Loris, A.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-02-17
- Volume
- 70
- Issue
- 6
- Pages
- 2219-2224
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W1975872053
- Cited by
- 158
- References
- 1
- FWCI
- 3.57
- Type
- journal article
- Language
- en
- Open access
- green
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