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Dynamic thiol exchange with ?-sulfido-?,?-unsaturated carbonyl compounds and dithianes.

ABSTRACT: A reversible covalent bond exchange of thiols, ?-sulfido-?,?-unsaturated carbonyls, and dithianes has been studied in DMSO and D(2)O/DMSO mixtures. The equilibrium between thiols and ?-sulfido-?,?-unsaturated carbonyls is obtained within a few hours, while the equilibration starting with the ?-dithiane carbonyls and thiols requires a few days. This time scale makes the system ideal for utilization in dynamic combinatorial chemistry.

SUBMITTER: Joshi G

PROVIDER: S-EPMC3472802 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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Dynamic thiol exchange with β-sulfido-α,β-unsaturated carbonyl compounds and dithianes.

Joshi Gururaj G Anslyn Eric V EV

Organic letters 20120830 18

A reversible covalent bond exchange of thiols, β-sulfido-α,β-unsaturated carbonyls, and dithianes has been studied in DMSO and D(2)O/DMSO mixtures. The equilibrium between thiols and β-sulfido-α,β-unsaturated carbonyls is obtained within a few hours, while the equilibration starting with the β-dithiane carbonyls and thiols requires a few days. This time scale makes the system ideal for utilization in dynamic combinatorial chemistry. ...[more]

PMID: 22934665

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