Mechanistic insights into Brønsted acid-induced nucleophilic substitution of aliphatic imidazole carbamate with halide ions
Tetrahedron Letters, ISSN: 0040-4039, Vol: 56, Issue: 11, Page: 1392-1396
2015
- 2Citations
- 6Usage
- 5Captures
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Metrics Details
- Citations2
- Citation Indexes2
- CrossRef1
- Usage6
- Abstract Views6
- Captures5
- Readers5
Article Description
Herein we report interesting reactivity of imidazole carbamate towards nucleophilic substitution with halide ions under Brønsted acidic conditions. Depending upon reaction conditions, halide ions could readily attack the carboxyl position and trigger decarboxylative alkyl halide formation. Alternatively, halide ions were also found to competitively undergo nucleophilic acyl substitution, which ultimately results in the generation of carbonate dimerization product.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/S0040403915001252; http://dx.doi.org/10.1016/j.tetlet.2015.01.098; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84923540665&origin=inward; https://linkinghub.elsevier.com/retrieve/pii/S0040403915001252; https://api.elsevier.com/content/article/PII:S0040403915001252?httpAccept=text/xml; https://api.elsevier.com/content/article/PII:S0040403915001252?httpAccept=text/plain; https://digitalcommons.lsu.edu/chemistry_pubs/576; https://digitalcommons.lsu.edu/cgi/viewcontent.cgi?article=1576&context=chemistry_pubs; https://repository.lsu.edu/chemistry_pubs/576; https://repository.lsu.edu/cgi/viewcontent.cgi?article=1576&context=chemistry_pubs; https://dx.doi.org/10.1016/j.tetlet.2015.01.098
Elsevier BV
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