Publication details
Reactions of 5-methylphenanthridinium iodide with nucleophiles and reaction products conversion.
| Authors | |
|---|---|
| Year of publication | 1993 |
| Type | Article in Periodical |
| Magazine / Source | Collection of Czechoslovak Chemical Communications |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | methylphenanthridinium; nucleophiles |
| Description | Reactions of 5-methylphenanthridinium iodide with nucleophiles and reaction products conversion.Reactions of 5-methylphenanthridinium iodide (I) with oxygen, nitrogen, and carbon nucleophiles, respectively. were studied. 5-Methylphenanthridinium iodide (I) yielded in the basic aqueous medium 5-methyl-6-phenanthridone (II) and 5.6-dihydro-5-methylphenanthridine (III). By NMR spectroscopy in the D2O-CD3CN solution 5,6-dihydro-6-deuteroxy-5-methylphenanthridine (IVb) (pseudobase) was observed as an immediate unstable product. 5-Methylphenanthridinium iodide (I) gave the corresponding adducts with methoxide and ethoxide anions, morpholine, piperidine, pyrrolidine, cyanide anion and acetone. Their structure was determined by IR. H-1 and C-13 NMR spectroscopy. Reactions of 5,6-dihydro-5-methyl-6-morpholinophenanthridine (VII) were followed by NMR spectroscopy. Morpholino adduct VII gave in the CD3CN-D2O solution pseudobase IVb and its products of disproportionation: oxophenanthridine II and dihydrophenanthridine III. Treatment of 5,6-dihydro-5-methyl-6-morpholinophenanthridine (VII) with H2O/D2O in (CH3)2CO/(CD3)2CO led to CH3COCH2-/CD3COCD2- adduct XIa/XIb formation, respectively. |