71089-33-3Relevant academic research and scientific papers
Influence of the Heterocyclic Side Ring on Orientation During Nitrations of 1,2-Alkylenedioxy-annelated Benzenes and Their Mononitro Derivatives
Takakis, Ioannis M.,Hadjimihalakis, Phaedon M.
, p. 625 - 634 (2007/10/02)
Nitration of 1,2-alkylenedioxybenzenes 1 furnished the respective nitro derivatives 3 and 4 in the relative ratios: 4a:3a/100:trace, 4b:3b/98:2.4, 4c:3c/86:14, 4e:3e/91:9, 4f:3f/99:1.3.Nitration of 4 gave 5a:6a:8a/0:0:100, 5b:6b:8b/7.7:3.2:89, 5c:6c:8c/23:12:65, 5d:6d:8d/14:74:12, 5e:6e:8e/27:18:55 and 5f:6f:8f/23:7.0:70.Nitration of the isomeric 3 afforded the dinitroproducts 5, 6 and 7 in the following relative ratios: 5a:6a:7a/92:8:0, 5b:6b:7b/80:20:0, 5c:6c:7c/69:20:11, 5d:6d:7d/45:19:36, 5e:6e:7e/37:57:5.9 and 5f:6f:7f/64:36:0.Nitration of 3-nitro-1,2-dimethoxybenzene (9) furnished: 10:11/63:37.Orientation as a function of the h eterocyclic ring-size is discussed.
Stereoelectronic Control of Aromatic Electrophilic Substitution. Importance of Independent Resonance Form Energies
Kruse, Lawrence I.,Cha, Jin K.
, p. 1333 - 1336 (2007/10/02)
Unexpected regiochemistry observed in the electrophilic substitution of polarized aromatic compounds is explained as occurring via a transition state which most closely resembles the valence-bond aromatic resonance form of lowest energy; electrophilic att
