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• W2024896188 abstract "Free radical reduction by tributylstannane of ω-iodopolyoxaalkyl acrylates derived from tri-, tetra-, penta-, hexa-, and heptaethylene glycols gives mixtures of uncyclized reduction products and macrocyclic ethers formed by endo cyclization. The rate constants for cyclization of the intermediate radicals at 80 °C in benzene were determined under carefully defined conditions to be 15 × 104, 13 × 104, 5.1 × 104, 10 × 104 and 3.6 × 104 s- 1, for formation of the 12-, 15-, 18-, 21- and 24-membered rings, respectively. These values indicate that the presence of oxygen atoms in the chains increases the rate by a factor of 10−30 by comparison with the previously reported cyclization of alkenyl species. The rate constants at 80 °C in benzene and the endo/exo ratio for reductive cyclizations of the methacrylate, crotonate, cinnamate, maleate, and fumarate esters of 8-iodo-3,6-dioxaoctanol have been determined. The reduction of the 8-iodo-3,6-dioxaoctyl acrylate in solvents of varying polarity indicated that the cyclization rate has a relatively low solvent dependence." @default.
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• W2024896188 date "1998-09-15" @default.
• W2024896188 modified "2023-09-25" @default.
• W2024896188 title "Formation of Macrocyclic Ethers by Free Radical Cyclization: Effects of Chain Length, Substituents, and Solvents" @default.
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• W2024896188 doi "https://doi.org/10.1021/jo980259o" @default.
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