V. Církva, O. Paleta
Apr 5, 1999
Citations
0
Influential Citations
18
Citations
Journal
Journal of Fluorine Chemistry
Abstract
The two-step synthesis of the diols is based on the radical addition of 2,2-dimethyl-1,3-dioxolane (1), a protected ethane-1,2-diol, to perfluoroalk-1-enes RF‐CF=CF2 (RF=CF3 ,C 9F19; 2, 3) and perfluoro[trifluorovinyl (poly)ethers] RFO‐CF=CF2 (RF=C3F7, C3F7O[CF(CF3)CF2], CF3(OCF2CF2)4; 4‐6) with preparative yields above 90% in each step. The additions were initiated photochemically or by dibenzoyl peroxide and were completely chemoselective and almost completely regioselective. 4-Fluoroalkylated dioxolanes obtained (7‐11) were deprotected by acid methanolysis to afford 1-polyfluoroalkylethane-1,2-diols (12‐16). 1,3-Dioxolane (27) or 2,2,4-trimethyl1,3-dioxolane (30) reacted at two centers to yield regioisomeric mixtures of fluoroalkylated dioxolanes. The factors influencing fluoroolefin and dioxolane regioselectivity are discussed. # 1999 Elsevier Science S.A. All rights reserved.