Crown ether catalyzed deuterium exchange in the synthesis of benzyl cyanides

✍ Scribed by Bruce Davis

• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: French
• Weight: 250 KB
• Volume: 24
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580240209

✦ Synopsis

N u c l e o p h i l i c s u b s t i t u t i o n o f benzyl-type c n l o r i d e s w i t h cyanide i o n i n deuterochloroform, deuteroacetoni t r i l e o r deuterobenzene c a t a l y z e d by 18-crown-6 r e s u l t s i n t h e i n t r o d u c t i o n o f deuterium onto t h e benzyl carbon. Benzyl cyanides a r e l a b e l l e d by r e f l u x i n g with cyanide i o n and crown e t h e r i n deutero solvent. Two such exchanges i n deuterochloroform produced g r e a t e r than 90% i n c o r p o r a t i o n . Side-chain l a b e l l e d phenylethylamine, tryptamine and ;and p t y r a m i n e were synthesized i n t h i s way.