Why are organotin hydride reductions of organic halides so frequently retarded? Kinetic studies, analyses, and a few remedies.
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Summary
The present work shows that the tacit but unproven assumption that the speed of reaction is determined by the slowest propagation step is rarely true for reductive chains and that the observed rate is in fact controlled by unseen side-reactions of propagating R(•) and Sn( •) radicals.
- Type
- article
- Published
- 2015-01-08
- Cited by
- 15
- References
- 78
- OpenAlex
- https://openalex.org/W1982517153
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:43391720
Keywords
Chemistry, Halide, Hydride, Kinetic energy, Organic chemistry
References
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- Catalysis of Radical Reactions: A Radical Chemistry Perspective.
- Katalyse von Radikalreaktionen: Konzepte aus Sicht der Radikalchemie
- Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement
- Understanding Initiation with Triethylboron and Oxygen: The Differences between Low-Oxygen and High-Oxygen Regimes.
- Why Not Trans? Inhibited Radical Isomerization Cycles and Coupling Chains of Lipids and Alkenes with Alkane -thiols.
- Radical chain repair: The hydroalkylation of polysubstituted unactivated alkenes
- Radical Arene Addition vs Radical Reduction: Why Organometal Hydride Chain Reactions Stop and How To Make Them Go.
- New Reactions with N-Heterocyclic Carbene Boranes and Amidine Boranes, and the Study of Initiators in the Radical Hydrostannation of Propargyl Silyl Ethers
- Investigating the structural chemistry of organotin(IV) compounds: recent advances
- Radical Reactions in Cavitands Unveil the Effects of Affinity on Dynamic Supramolecular Systems.
- Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction
- Transition Metal Free Stannylation of Alkyl Halides: The Rapid Synthesis of Alkyltrimethylstannanes.
- Photoinduced B-H Arylation of N-Heterocyclic Carbene Boranes with Sulfonyl(hetero)arenes.
- Recent Advances in Photoredox‐Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction
- Di‐ Tert ‐Butyl Hyponitrite
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