Synthesis of 1 - deuterioaldehydes from methylene - BIS - pyridinium cations

✍ Scribed by R. A. Olofson; D. M. Zimmerman; Rodney C. Schnur

• Publisher: John Wiley and Sons
• Year: 1972
• Tongue: French
• Weight: 341 KB
• Volume: 8
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2590080305

✦ Synopsis

A synthesis o f I-deuterio a n d I-tritioaldehydes, especially arylaldehydes, from precursor gem-diha-

Zides i s described. The scheme i s especially useful when high label incorporation is desired.

INTRODUCTION.

We r e p o r t h e r e the experimental p r o c e d u r e for a cdnvenient and economical p r e p a r a t i o n of 1 -deuterio o r 1 -tritiobenzaldehyde and other labelled aldehydes of high isotopic purity. the r e l a t e d --dihalides a r e inexpensive o r r e a d i l y availablep r i m a r i l y benzal type halides which a r e often favored c o m m e r c i a l p r e c u r s o r s of the unlabelled arylaldehydes.

IIa) and hydrolysis of the known benzal-=-pyridinium dibromide (Ia) to benzaldehyde-1-d, h a s been outlined in a p r e l i m i n a r y communication, 6, ')