Betaines derived from amino and hydrazino acids as phase transfer catalysts

✍ Scribed by Yuri Goldberg; Edgars Ābele; Gunārs Bremanis; Pēteris Trapenciers; Alexander Gaukhman; Juris Popelis; Artur Gomtsyan; Ivars Kalviņš; Mariya Shymanska; Edmunds Lukevics

• Book ID: 104204919
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 745 KB
• Volume: 46
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)89759-3

✦ Synopsis

Betaines derived from o-, B-and y-amino acids (obtained by alkylation of the corresponding amino acids with 0-methyl-N,N'diisopropylisourea) as well.as B-hydrazino acids (prepared-by dehydrohalogenative hydrolysis of methyl 3-(Z-alkyl-2,2-dimethylhydrazinium)propionate halides catalyse typical phase transfer reactions (dichlorocyclopropanation of styrene, N-formylation of pyrrolidine, dehydration of benzamide and phenylacetamide, Williamson synthesis of benzyl propyl ether, addition of ethoxycarbonylnitrene to 2,3-dimethylbutene-2.

In most cases, the activity of zwitterionic salts is at least similar to that of tvoical phase transfer catalvsts (tetraalkylammonium salts). The mechanism of the catalytic act:on of betaines is proposed.