Amidoethylation of Anthracene Hydride by N-Aroylaziridines: Inner-sphere Single Electron Transfer (SET) and Radical Coupling confirmed

Nucleophilic ring opening of aziridines

“…Similarly, while indole-Li and 124-S provide only normal N-substitution in THF/ether in accord with a reaction of the highly nucleophilic N-anion, in toluene (no dissociation) this product arises in 29% yield only while substitution in position 3 (very poor Nu -) proceeds with 49% abnormal and 16% normal NRO [71]. The said hypothesis on the abnormal NRO [76] consisted of SET, homolytic ring opening and radical coupling or more complicated processes as realized in reactions of Trwith Az's 124-A (even with 124-Aa) [78] whose three Tr containing products are shown in Sche- [84] no difference in RS for 124-A or other acylaziridines is so far known between products of real NRO and those from all kinds of pseudo NRO but one should be aware that a conformation dependent stereoelectronic effect (cf. [8]) may change RS of homolytic ring opening for trans-Az's of type trans-109b.…”

Benzylic Fragmentation (BFR), an Aromatic Analogue of E1cB Including a Homolytic Variant, as either Nucleofugal or Homolytic Path to Aryl Stabilized Carbanions or Ketyls, respectively

“…1-Benzoyl-2-methylaziridine yields a mixture (14 -18% + 47 -58%) of n-and i-propylbenzamide [13]. The carbonyl attack 17 → 18 is reversible [14,9,10] and influenced by the counterion [14]; isolation of 24 is clear evidence for this attack.…”