e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521
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…
Index: Branchi, Barbara; Galli, Carlo; Gentili, Patrizia; Marinelli, Manuela; Mencarelli, Paolo European Journal of Organic Chemistry, 2000 , # 14 p. 2663 - 2668
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 ...
[Bryce, Martin R.; Davies, Stephen R.; Grainger, Andrew M.; Hellberg, Jonas; Hursthouse, Michael B.; et al. Journal of Organic Chemistry, 1992 , vol. 57, # 6 p. 1690 - 1696]
