What question did this study set out to answer?

Determine the stereochemical pathway and chemical mechanism responsible for the transformation of cinnamic acid dibromide into β-bromostyrene.

June 1, 1953Journal of the American Chemical Society

The Stereochemistry and Mechanism of the Transformation of Cinnamic Acid Dibromide to β-Bromostyrene1

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Authors

EGErling GrovensteinGeorgia Institute of Technology DLDonald E. LeeUniversity of California, Irvine

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Implication

Mechanistic study uncovers the stereochemical pathway of cinnamic acid dibromide decomposition, indicating stereospecific decarboxylative elimination.

Key Points

Determine the stereochemical pathway and chemical mechanism responsible for the transformation of cinnamic acid dibromide into β-bromostyrene.
Examined the conversion of cinnamic acid dibromide isomers under controlled reaction conditions.
Tracked the stereochemical configuration and isomeric purity of the resulting β-bromostyrene products.
The conversion proceeds through a stereospecific decarboxylative elimination pathway.
The geometric configuration of the starting dibromide dictates the cis- or trans-alkene geometry of the β-bromostyrene product.

Cite This Study

Grovenstein et al. (1953) studied this question.

synapsesocial.com/papers/6a8bbae89d5fb440a3beb629 https://doi.org/10.1021/ja01107a025

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Implication

Mechanistic study uncovers the stereochemical pathway of cinnamic acid dibromide decomposition, indicating stereospecific decarboxylative elimination.

The Stereochemistry and Mechanism of the Transformation of Cinnamic Acid Dibromide to β-Bromostyrene1

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Implication

Key Points

Cite This Study

The Stereochemistry and Mechanism of the Transformation of Cinnamic Acid Dibromide to β-Bromostyrene1

Discussion

Member takes

Implication

Key Points

Cite This Study

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