On the Configurational Stability of α-Lithiated Sulfurated Styrene Oxides: Synthetic and Mechanistic Aspects

Abstract

The configurational stability of some sulfurated styrene oxides has been investigated. Chemical studies have shown that in THF at 157 K α-lithiated ortho- and para-phenylthiostyrene oxides are configurationally unstable and undergo a fast racemization on the time scale of the reaction, whereas α-lithiated meta-phenylthiostyrene oxide retains its stereochemical integrity for at least 60 min. The deprotonation-trapping methodology has also been employed for the preparation of a sulfurated β-aminoalcohol effective for the fight against phytopathogenic fungi.

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Keywords:

• Configurational stability
• oxiranyllithiums
• racemization
• sulfurated styrene oxides