Cyclization and Ring-Expansion Processes Involving Samarium Diiodide Promoted Reductive Formation and Subsequent Oxidative Ring Opening of Cyclopropanol …

…, M Tamura, E Hasegawa

Index: Tsuchida, Hiroyuki; Tamura, Mutsuko; Hasegawa, Eietsu Journal of Organic Chemistry, 2009 , vol. 74, # 6 p. 2467 - 2475

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Citation Number: 25

Abstract

Samarium diiodide promoted reaction of various α-bromomethyl cycloalkanones, followed by subsequent treatment with trimethylsilyl chloride, leads to the production of cyclopropyl silyl ethers embedded in bicyclo [m. 1.0] alkane frameworks. Treatment of the ethers with oxidative electron-transfer reagents, such as Fe (III), Ce (IV), and Mn (III) salts, generates ring-expanded ketones that convert to cyclic conjugated enones in moderate to good ...