Generation of sec-thioamide dianions and their regioselective reaction with electrophiles.

✍ Scribed by Y. Tamaru; M. Kagotani; Y. Furukawa; Y. Amino; Z. Yoshida

• Book ID: 104234251
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 194 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81919-5

✦ Synopsis

The enolates of see-thioamides j3, which are generated by three different methods (scheme II and equation l), are alkylated selectively at the c-carbon to the thiocarbonyl group. The unusual i3 '-lithiation to provide an intermediate $i is observed for N-methyl-a,B-dimetylthioacrylamide and N-methylthiocyclohexenecarboxamide.