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Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs.

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.

SUBMITTER: Lujan-Montelongo JA

PROVIDER: S-EPMC4520545 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs.

Lujan-Montelongo J Armando JA Estevez Angel Ojeda AO Fleming Fraser F FF

European journal of organic chemistry 20150301 7

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. ...[more]

PMID: 26236153

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