By Jacques Mortier
Prepared to permit scholars and artificial chemists to appreciate and extend on fragrant reactions coated in beginning classes, the ebook deals a radical and available mechanistic clarification of fragrant reactions concerning arene compounds.
• Surveys equipment used for getting ready arene compounds and their transformations
• Connects reactivity and method with mechanism
• Helps readers observe fragrant reactions in a realistic context via designing syntheses
• Provides crucial information regarding ideas used to figure out response mechanisms
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Additional info for Arene chemistry : reaction mechanisms and methods for aromatic compounds
A subsequent NMR study involving the low‐temperature ethylation of 1,3,5‐ triethylbenzene also revealed the presence of σ‐complex intermediates [65a]; however, isomeric species were formed rapidly by hydride/alkyl shifts. Indeed, this aspect of cyclohexadienyl cation chemistry has made the study of σ‐complexes difficult, as the barrier for isomerization is often quite low. 24 Intermediate σ‐complexes and the conversion to Friedel–Crafts products. Likewise, the isomerization of the σ‐complex 83 was observed in solution phase .
The ring‐Br2 bond distance is found to be less than the van der Waals radii, consistent with a weak donor–acceptor interaction within the π‐complex. Analysis also shows there is little Br─Br bond elongation observed and the C─H bonds remain within the ring plane. Upon warming the π‐complex crystals to −78°C, HBr is released and bromobenzene is formed quantitatively . A similar π‐complex was obtained with Br2 and toluene at −150°C . Two structures were observed from the crystalline products: a π‐complex with Br2 located near the ortho carbon (58) and a π‐complex with Br2 located near the para carbon (59).
With the uncomplexed nitrosonium ion, N─O stretch is observed at 2272 cm−1, while the [NO, hexamethylbenzene]+ π‐ complex exhibits a stretch at 1885 cm−1 . 15 Å and an N─O stretch frequency of 1876 cm−1. These data indicate a significant degree of electron transfer in the π‐complex; however, the complexes are ESR silent, suggesting the nitric oxide and hexamethylbenzene radical cation are not fully formed species. The [NO, hexamethylbenzene]+ π‐complex has also been studied by UV–Vis and NMR spectroscopy .