CARBONYLATION OF TRICHLOROACETALDEHYDE (CHLORAL) IN CONCENTRATED SULFURIC-ACID - STEREOCONTROLLED SYNTHESIS OF CIS-2,5-BIS(TRICHLOROMETHYL)-1,3-DIOXOLAN-4-ONE AND TRANS-2,5-BIS(TRICHLOROMETHYL)-1,3-DIOXOLAN-4-ONE

Authors
MORI S EMURA K KANO M KUDO K KOMATSU K SUGITA N
Citation
S. Mori et al., CARBONYLATION OF TRICHLOROACETALDEHYDE (CHLORAL) IN CONCENTRATED SULFURIC-ACID - STEREOCONTROLLED SYNTHESIS OF CIS-2,5-BIS(TRICHLOROMETHYL)-1,3-DIOXOLAN-4-ONE AND TRANS-2,5-BIS(TRICHLOROMETHYL)-1,3-DIOXOLAN-4-ONE, Tetrahedron, 51(33), 1995, pp. 8977-8982
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
33
Year of publication
1995
Pages
8977 - 8982
Database
ISI
SICI code
0040-4020(1995)51:33<8977:COT(IC>2.0.ZU;2-W
Abstract
Carbonylation of trichloroacetaldehyde(chloral) in concentrated sulfur ic acid readily gave 2,5-bis(trichloromethyl)-1,3-dioxolan-4-ones (cis and trans) and 3,3,3-trichloro-2-hydroxypropanoic acid. The cis isome r was isolated for the first time, and confirmed by Xray structural an alysis. The cis/trans ratio of dioxolanones largely depended upon the concentration of sulfuric acid. Highly diastereoselective formation of the dioxolanones was achieved with 99wt% sulfuric acid (cis : trans = 95 : 5) or with 90wt% sulfuric acid (0 : 100).