PREPARATION OF ALPHA-SUBSTITUTED ACROLEINS VIA THE REACTION OF ALDEHYDE OR THE CORRESPONDING OZONIDE WITH DIHALOMETHANE AND DIETHYLAMINE

Authors
HON YS CHANG FJ LU L LIN WC
Citation
Ys. Hon et al., PREPARATION OF ALPHA-SUBSTITUTED ACROLEINS VIA THE REACTION OF ALDEHYDE OR THE CORRESPONDING OZONIDE WITH DIHALOMETHANE AND DIETHYLAMINE, Tetrahedron, 54(20), 1998, pp. 5233-5246
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
20
Year of publication
1998
Pages
5233 - 5246
Database
ISI
SICI code
0040-4020(1998)54:20<5233:POAAVT>2.0.ZU;2-8
Abstract
Treatment of aldehydes or the corresponding ozonides with a mixture of dibromomethane and diethylamine afforded alpha-substituted acroleins in modest to good yields. The beta-carbon of the acrolein (nc, n = 1-1 6) derived from dibromomethane. Functional groups, such as ketone, hyd roxy, acetoxy, bromide, iodide, ester are compatible with this reactio n condition. The relative rates and yields of this transformation in d ichloromethane were found to be in the following order: CH2I2 > CH2Br2 > CH2Cl2. (C) 1998 Published by Elsevier Science Ltd. All rights rese rved.