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 paraphenylthiostyrene 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.
On the Configurational Stability of alpha-Lithiated Sulfurated Styrene Oxides: Synthetic and Mechanistic Aspects
CAPRIATI, Vito;PERNA, FILIPPO;Salomone, A.
2011-01-01
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 paraphenylthiostyrene 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.File in questo prodotto:
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