Related Products of 19472-74-3, As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 19472-74-3, Name is 2-Bromophenylacetonitrile, SMILES is C1=C(C(=CC=C1)CC#N)Br, belongs to nitriles-buliding-blocks compound. In a article, author is Feberero, Claudia, introduce new discover of the category.
Experimental and Computational Study of the 1,5-O -> N Carbamoyl Snieckus-Fries-Type Rearrangement
The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O -> N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O -> N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized O-arylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.
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