The [1,5]-Brook rearrangement: An initial application in anion relay chemistry

Amos B. Smith; Ming Xian; Won Suk Kim; Dae Shik Kim

doi:10.1021/ja065033e

The [1,5]-Brook rearrangement: An initial application in anion relay chemistry

Amos B. Smith, Ming Xian, Won Suk Kim, Dae Shik Kim

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

66 Scopus citations

Abstract

The [1,5]-Brook rearrangement proceeds efficiently in a series of hydroxyl dithiane substrates with sodium and potassium bases; less effective are lithium bases. That the mode of silyl migration is intramolecular was demonstrated by a crossover experiment. Finally, the tricomponent anion relay chemistry (ARC) coupling tactic was demonstrated employing the [1,5]-Brook rearrangement.

Original language	English
Pages (from-to)	12368-12369
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	38
DOIs	https://doi.org/10.1021/ja065033e
State	Published - 27 Sep 2006

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abstract = "The [1,5]-Brook rearrangement proceeds efficiently in a series of hydroxyl dithiane substrates with sodium and potassium bases; less effective are lithium bases. That the mode of silyl migration is intramolecular was demonstrated by a crossover experiment. Finally, the tricomponent anion relay chemistry (ARC) coupling tactic was demonstrated employing the [1,5]-Brook rearrangement.",

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AU - Xian, Ming

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AU - Kim, Dae Shik

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AB - The [1,5]-Brook rearrangement proceeds efficiently in a series of hydroxyl dithiane substrates with sodium and potassium bases; less effective are lithium bases. That the mode of silyl migration is intramolecular was demonstrated by a crossover experiment. Finally, the tricomponent anion relay chemistry (ARC) coupling tactic was demonstrated employing the [1,5]-Brook rearrangement.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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The [1,5]-Brook rearrangement: An initial application in anion relay chemistry

Abstract

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