Mechanism and Unusual Fragmentation Selectivities of Aryltrialkylstannane Cation Radicals

The Journal of Organic Chemistry
Pu Luo, Joseph P Dinnocenzo

Abstract

Aryltrialkylstannane cation radicals were generated and characterized by nanosecond transient absorption spectroscopy. Kinetics show the fragmentations of the stannane cation radicals occur by a bimolecular, nucleophile-assisted mechanism (S(N)2). Consistent with this hypothesis, steric effects on both the nucleophile and the stannane cation radicals were observed. Steady-state, preparative photooxidation experiments show that aryltrimethylstannane cation radicals have an unusual preference for loss of aryl radicals over methyl radicals and that the selectivity for aryl vs methyl radical loss is dependent on the identity of the nucleophile. The preference for loss of aryl radicals is rationalized by a hypothesis based on Bent's rules.

References

Sep 27, 2001·Journal of the American Chemical Society·H J de LijserJ P Dinnocenzo
Oct 25, 2001·The Journal of Organic Chemistry·Brian E. Love, Edward G. Jones
Aug 20, 2003·Inorganic Chemistry·J Christopher Thomas, Jonas C Peters
Oct 28, 2004·Journal of the American Chemical Society·Gonzalo GuiradoJoseph P Dinnocenzo
Sep 4, 2014·The Journal of Organic Chemistry·Pu LuoJoseph P Dinnocenzo

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Citations

Jun 13, 2020·The Journal of Organic Chemistry·Elizabeth C Feinberg, Joseph P Dinnocenzo

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