The reactions of n-benzoylperoxycarbamic acid with azines and imines

✍ Scribed by Rodrigo Paredes; Holger Bastos; Raul Montoya; Alba Lucia Chavez; William R. Dolbier Jr.; Conrad R. Burkholder

• Book ID: 104203803
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 923 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86210-4

✦ Synopsis

N-Renzoylperoxycarbamic acid (BPC) was found to react generally with imines and asines to form oxasiridines rather than N-oxides. The imine products were stable, but those found from asines apparently were unstable and converted to ketones or aldehydes plus diazo compounds. N-Bensoylperoxycarbamic acid &SC) has been reported by Rebek et al. to be an effective epoxidation agent, with an advantage over typical peracids that it yielded as co-products only neutral moieties.' This made it a potentially very useful reagent when dealing with acid-sensitive systems. We have in the past been interested in the thermal reactivity and photochemistry of asine monoxides 2 and thus have been interested in new, potentially useful oxygen transfer reagents for the synthesis thereof. In this regard, we found that txrffered trifluoroperacetic acid was useful in the preparation of a number of phenyl-substituted azine monoxides, i.e. k and P, while for the alkyl-substituted analogues, only decomposition products could be obtained.2 Other workers, before and since, have also attempted peroxyacid oxidations of arines with similar results.3r4 -RR'C=N-N=CRR' ~H.~%Sf?J P