What question did this study set out to answer?

To examine the stereochemical outcomes and cleavage mechanisms during acid-catalyzed addition reactions to stilbene and styrene oxides.

December 1, 1965The Journal of Organic Chemistry

Stereochemistry of the Additions of Acids to Stilbene and Styrene Oxides1

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Authors

GBGiancarlo BertiUniversity of Pisa FBF. BottariUniversity of Pisa PFPier Luigi FerrariniUniversity of Florence

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Implication

Experimental study reveals stereospecific cleavage during acid addition to stilbene and styrene oxides, indicating predictable geometric control in epoxide ring opening.

Key Points

To examine the stereochemical outcomes and cleavage mechanisms during acid-catalyzed addition reactions to stilbene and styrene oxides.
Subjected isomeric stilbene oxides and styrene oxides to ring-opening reactions using various protic and Lewis acids.
Isolated and characterized the geometric and stereoisomeric configurations of the resulting addition adducts.
Acid addition proceeded with characteristic stereoselectivity dictated by the epoxide structure and the electronic nature of the attacking acid.
Cleavage pathways revealed competing inversion and retention mechanisms driven by carbocation stability and steric constraints at the benzylic carbons.

Cite This Study

Berti et al. (1965) studied this question.

synapsesocial.com/papers/6a9c2f5ac1d4b3b2fc0e4804 https://doi.org/10.1021/jo01023a026

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Implication

Experimental study reveals stereospecific cleavage during acid addition to stilbene and styrene oxides, indicating predictable geometric control in epoxide ring opening.

Stereochemistry of the Additions of Acids to Stilbene and Styrene Oxides1

Discussion

Member takes

Implication

Key Points

Cite This Study

Stereochemistry of the Additions of Acids to Stilbene and Styrene Oxides1

Discussion

Member takes

Implication

Key Points

Cite This Study

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