Oxidative coupling reactions under PTC conditions

✍ Scribed by V.N. Gogte; A.A. Natu; V.S. Pandit

• Book ID: 104221601
• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 186 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88280-5

✦ Synopsis

Succinic acid derivatives have been prepared from cyanohalides under PTC conditions in good yields. Substitution of primary halides by CN-under PTC conditions has been one of the most thoroughly studied reactions? However, there is little information available in the literature regarding the substitution of secondary and tertiary halides by CN-. We happened to try out the substitution of some secondary and tertiary halides by CN-under PTC conditions wherein we came across new oxidative coupling reactions, which are described in present communication. In the course of further work, it was later found that these reactions can even be carried out in the absence of CN-. a(-Bromobenzylcyanide3 1, failed to react with NaCN in benzene, in presence of TEBA. However, when this reaction was carried out by using 50% aq. NaOH solution (ion pair extraction technique)4 using TEBA, trans 1,2-dicyano-1,2_diphenylethylene 2 was obtained in good yield.