A Radical and An Electron Transfer Process Are Compared in Their Regioselectivities Towards A Molecule with Two Different C− I Bonds: Effect of Steric Congestion

B Branchi, C Galli, P Gentili, M Marinelli…

文献索引：Branchi, Barbara; Galli, Carlo; Gentili, Patrizia; Marinelli, Manuela; Mencarelli, Paolo European Journal of Organic Chemistry, 2000 , # 14 p. 2663 - 2668

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被引用次数: 5

摘要

Abstract Steric compression in 1, 4-diiodo-2, 6-dimethylbenzene (2a) makes the C− I bond flanked by methyls substantially weaker (a buttressing effect) than the unhindered C− I bond. Calculations also confirm the weaker bonding interaction of the hindered C− I bond of 2a. This causes a remarkable regioselectivity toward the weaker bond in dehalogenation by stannyl radicals. Conversely, a much lower regioselectivity is found for a process− a ...