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- W2013156617 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 photostimulated SRN1 reaction with the enolate ion of a ketone − which requires the conversion of 2a into a radical anion. A calculation of the BDE of the C−I bond for aa ArI•− system is offered. Finally, the hindered aryl radical intermediate resulting from cleavage of the weaker C−I bond of 2a•− shows a modest but detectable discrimination between reduction or substitution, this once again being due to the steric congestion." @default.
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- W2013156617 date "2000-07-01" @default.
- W2013156617 modified "2023-09-27" @default.
- W2013156617 title "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" @default.
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- W2013156617 doi "https://doi.org/10.1002/1099-0690(200007)2000:14<2663::aid-ejoc2663>3.0.co;2-y" @default.
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