- peri-Naphthylenediamines 36. 5,6-Bis(dimethylamino)acenaphthylene in [4+2] cycloaddition reactions. Synthesis and characteristic features of protonation of "proton sponges" with the 8,9-diazafluoranthene structure
-
5,6-Bis(dimethylamino)acenaphthylene is readily involved in [4+2] cycloaddition reactions with symm-tetrazine derivatives to form new "proton sponges" with the diazafluoranthene skeleton. Under analogous condition, 1,8-bis(dimethylamino)-4-vinylnaphthalene gave 4-pyridazinyl derivatives. The relative reactivities of 5,6-bis(dimethylamino)acenaphthylene, 1,8-bis(dimethylamino)-4-vinylnaphthalene, 5-dimethylaminoacenaphthylene, and acenaphthylene in the reactions with 3,6-diphenyl-symm-tetrazine are in a ratio of 32:17:14:1. The site of protonation of 3,4-bis(dimethylamino)-7,10-diphenyl- 8,9-diazafluoranthene is controlled by the basicity of the solvent. The reaction in acetonitrile afforded the cation stabilized by an intramolecular hydrogen bond, whereas the reaction in dimethyl sulfoxide gave rise to the resonance-stabilized cation. 6,7-Bis(dimethylamino)phenalen-1-one was protonated only at the carbonyl group.
- Pozharskii,Ozeryanskii,Vistorobskii
-
-
Read Online