ChemInform Abstract: Remarkable Dependence of the Regioselectivity of Free Radical Additions to 3-Cinnamoyloxazolidin-2-ones on the Stability of the Intermediate Adduct-Radical, Electrophilicity of the Adding Radicals and the Conditions for Their Generation.

✍ Scribed by V. I. TARAROV; N. YU. KUZNETZOV; V. I. BAKHMUTOV; N. S. IKONNIKOV; Y. N. BUBNOV; V. N. KHRUSTALEV; T. F. SAVELEVA; Y. N. BELOKON

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 43 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199811079

✦ Synopsis

Remarkable Dependence of the Regioselectivity of Free Radical Additions to 3-Cinnamoyloxazolidin-2-ones on the Stability of the Intermediate Adduct-Radical, Electrophilicity of the Adding Radicals and the Conditions for Their Generation.

-The addition of nucleophilic and electrophilic radicals to the double bond of 3cinnamoyloxazolidinones [cf. (I)] is studied. The electrophilic radical CCl 3 adds regioselectively at the α-position of the double bond to afford a diastereomeric mixture of 2'-trichloromethyl-3'-phenylpropionyloxazolidinones (III) and (IV) independent of the type of radical initiation. In contrast, the addition of the nucleophilic isopropyl radical to compound (I) occurs at the α-as well as the β-position of the double bond. While at high temperatures the α-attack is favoured affording the diastereomers (VI) and (VII), β-addition becomes the predominating process at low temperatures yielding diastereomers (VIII) and (IX). -(TARAROV, V. I.;