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

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

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.",

author = "Smith, \{Amos B.\} and Ming Xian and Kim, \{Won Suk\} and Kim, \{Dae Shik\}",

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AU - Smith, Amos B.

AU - Xian, Ming

AU - Kim, Won Suk

AU - Kim, Dae Shik

PY - 2006/9/27

Y1 - 2006/9/27

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/33749173658

U2 - 10.1021/ja065033e

DO - 10.1021/ja065033e

M3 - Article

C2 - 16984158

AN - SCOPUS:33749173658

SN - 0002-7863

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SP - 12368

EP - 12369

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 38

ER -

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

Abstract

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