Benzylic structure

Hydantoin — see also Imidazolidine-2,4-dione Hydantoin, 3-aryl-5-benzyl-structure, 5, 351... 

Figures 19.1 and 19.2 are the mass spectra for the aromatic isocyanates. Losses of 28 (CO) and 29 (H + CO) Daltons are observed. The intensity of m/z 91 (M-NCO) ion favors the benzyl structure in Figure 19.1.

Two significant results of that investigation were that deuterium incorporation was found to vary with product fraction and that preferential incorporation of deuterium was found in benzylic structural positions. The purpose of this research is to extend the use of the deuterium tracer method to donor solvent reactions. 

In 2001, Knaack and co-workers56 reported an application of the INADEQUATE experiment in the course of synthesizing and characterizing a biologically active 2-[l-(4-chlorobenzyl)-lH-indol-3-yl]-2-oxo-N-pyri-din-4-yl acetamide (6). Treatment of l-(4-chlorobenzyl)-lH-indole with oxalyl chloride afforded the corresponding oxoacetyl chloride that was finally subjected to aminolysis with 4-aminopyridine to afford the final product of the reaction scheme, 6. Although the NMR data supported the N-benzyl structure, a 1,1-ADEQUATE spectrum was acquired to provide additional confirmation of the structure of 6. 

In the case of reaction with trihydroxyethylamine (THEA), the quaternary ammonium undergoes an intramolecular rearrangement leading to an amino ether (Scheme 23), which can react with another benzylic structure to form a quaternary ammonium salt responsible for crosslinking (10). 

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