A-Acetoxydibenzylnitrosamine

The chemical activation of dibenzylnitrosamine (VI), that is the chemical conversion to the a-acetoxy derivative, would give an intermediate which on hydrolysis would yield the benzylcar-bocation. Hius on the basis of the previous report (, ) the a-acetoxydibenzylnitrosamine (VII) should be a non-mutagenic, non-carcinogenic nitrosamine. 

The introduction of an activating system, such as an S-9 microsomal fraction, led to a decrease in the potency of VII as a mutagen. Although this was not consistent with the results reported by Camus, Wiessler, Molaveille, and Bartsch ( ) for acetoxymethyl- butylnitrosamine (V), it did seem to be consistent with the postulate that hydrolysis of the acetoxy group would be catalyzed by the activating S-9 system through an esterase activity. This in turn would deactivate the a-acetoxydibenzylnitrosamine (VII) before it would act as an electroj ile with nucleic acids. 

The spectral data provide information about the structure of a-acetoxydibenzylnitrosamine (VII). The high frequency (1780 cm ) for the carbonyl group in the infrared spectrum (Fig. 9) is consistent with this structure ( ) and the introduction of the chiral center at the benzylic position causes the methylene of the other benzyl ic substituent to be diastereotopic and appear in the nmr spectrum as an AB quartet. The center of the quartet... 

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