Tetrahedron p. 8977 - 8982 (1995)
Update date:2022-09-26
Topics:
Mori, Sadayuki
Emura, Kazuhiro
Kano, Motoaki
Kudo, Kiyoshi
Komatsu, Koichi
Sugita, Nobuyuki
Carbonylation of trichloroacetaldehyde(chiral) in concentrated sulfuric 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 isomer was isolated for the first time, and confirmed by X-ray structural analysis. 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).
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