Polyaromatic imines

The stereochemistry of the Staudinger reaction was highlighted [86] using as substrates polyaromatic imines and acetoxy, phenoxy, or phthalimido acid chloride. The stereochemistry of the resulting p-lactams seemed to vary depending on the substituents present in the imines and the acid chlorides. For instance, if the polyaromatic moiety was linked to the iminic nitrogen, the reaction produced //Y/n.v-p-lactams if the same moiety was linked to the iminic carbon, cA-p-lactams were isolated. 

Lactams with polyaromatic substituents at C-4 have been reported to be synthesized, via Staudinger reaction [99]. The reaction of polyaromatic imines with acetoxy, phenoxy and phthalimido acid chloride in the presence of triethylamine at... 

Synthesis of Novel (5-Lactams with Polyaromatic Imines... 

A highly stereoselective synthesis of 3-pyrrole-substituted fi-lactams 15 and 16 is reported via -lactams 13 and 14 obtained through treatment of imines 11 derived from N-phenyl, p-methoxyphenyl, or 6-chrysenyl amine with phthalimido acetic acid 12 and deprotection of phthalimido group by ethylenediamine, respectively [42]. The polyaromatic imines derived from 6-chrysenyl amine produced (+)-tra s isomer exclusively (Scheme 3.8). The electron-withdrawing aromatic groups at the C- and N-termini of the imine led to the formation of the trans isomer. The formation of trans isomer in the case of N-chrysenyl imines and N-diaryl imines... 

Hall HK Jr, Padias AB, Williams PA, Gosau J-M, Bomie HW, Park D-K (1995) Novel polyaromatic quinone imines. Macromolecules 28 1-8... 

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