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BIBTEX RIS

Reaction of Ethyl α-Chloro-α-phenylselenoacetate with Alkenes: Synthesis of α-Phenylseleno-γ-Butyrolactones

1995; Thieme Medical Publishers (Germany); Volume: 1995; Issue: 10 Linguagem: Inglês

10.1055/s-1995-4101

1437-210X

Cláudio C. Silveira, Marcelo Augusto de Araújo, Eder J. Lenardão, Antônio L. Braga, Miguel J. Dabdoub,

Molecular Spectroscopy and Structure

Ethyl α-chloro-α-phenylselenoacetate (1) reacts with alk-1-enes in the presence of TiCl4 to give the corresponding α-phenylseleno γ,δ-unsaturated esters. Reaction of 1 with di- and trisubstituted alkenes and SnCl4 as a Lewis acid affords γ-butyrolactones directly and a minor amount of the γ,δ-unsaturated esters. These esters were converted into γ-butyrolactones on hydrolysis and reaction with electrophiles.