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Silver-mediated allylic disulfide rearrangement for conjugation of thiols in protic media.

ABSTRACT: Alkyl and aryl allyl disulfides are induced to undergo the desulfurative allylic rearrangement by silver nitrate in protic solvents at room temperature, thereby removing the necessity for the use of phosphines as thiophilic reagents. The silver-mediated reaction functions at ambient temperature in protic solvents and in the absence of protecting groups.

SUBMITTER: Crich D

PROVIDER: S-EPMC2852026 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Silver-mediated allylic disulfide rearrangement for conjugation of thiols in protic media.

Crich David D Subramanian Venkataraman V Karatholuvhu Maheswaran M

The Journal of organic chemistry 20091201 24

Alkyl and aryl allyl disulfides are induced to undergo the desulfurative allylic rearrangement by silver nitrate in protic solvents at room temperature, thereby removing the necessity for the use of phosphines as thiophilic reagents. The silver-mediated reaction functions at ambient temperature in protic solvents and in the absence of protecting groups. ...[more]

PMID: 19911776

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