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Accepted (AM)Open Access (License Unspecified), Open
Journal article
Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs
European journal of organic chemistry, v 2015(7), pp 1602-1605
Mar 2015
PMCID: PMC4520545
PMID: 26236153
Abstract
Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.
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Details
- Title
- Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs
- Creators
- J. Armando Lujan-Montelongo - IPN, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07360, DF, MexicoAngel Ojeda Estevez - Duquesne UniversityFraser F. Fleming - Duquesne University
- Publication Details
- European journal of organic chemistry, v 2015(7), pp 1602-1605
- Publisher
- Wiley
- Number of pages
- 4
- Grant note
- CONACYT; Consejo Nacional de Ciencia y Tecnologia (CONACyT) R15AI051352 / NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of Allergy & Infectious Diseases (NIAID) 2R15AI051352-04 / NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000349973500028
- Scopus ID
- 2-s2.0-84923229274
- Other Identifier
- 991020898500404721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic