Journal
TETRAHEDRON LETTERS
Volume 42, Issue 32, Pages 5565-5569Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)00958-3
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Initial rate studies of samarium diiodide mediated reduction of 3-heptanone to 3-heptanol are reported. The reduction of 3-heptanone with the polydentate tri(ethylene glycol) methyl ether is 16 times faster than without a proton donor, and 4.3 times faster than methanol. The primary kinetic isotope effect (KIE) was measured as k(H)/ k(D) approximate to 2, indicating a rate-determining proton transfer. Diols are superior to mono-alcohols as proton donors, the reduction of 3-heptanone is 255 times as fast with di(ethylene glycol) than in the absence of a proton donor. A mechanism of glycol accelerated samarium. diiodide reduction is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.
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