Notestalline hydrochloride, mp 298-300°dec (lit.7 mp 300°d ec), M26d (EtOH) +207°.(+)-Nandigerine (10) from (+;-A7-Methylnandigerine (8).-The usual conditions afforded 10 (22% from 8), isolated as the crystalline hydrochloride, mp 242-245°dec (lit.7 mp 245-247°d ec), [<*] 26d (EtOH) +240°.( + )-Hernovine ( 11) from (+ )-A7-Methylhemovine ( 9).-The usual conditions afforded 11 (18% from 9) as crystals, mp 235-237°dec (lit.7 mp 236-240°d ec), [a] 26d (EtOH) +253°.Reaction of A7-Oxide 2 with Sulfur Dioxide in Methanol-Benzene.-Dried A7-oxide 2 (50 mg) was dissolved in 1:1 methanol-benzene (20 ml) and S02 was passed into the mixture for 0.5 hr. Aqueous hydrochloric acid (2 N, 10 ml) was added and the solution was refluxed for 3 hr. Basification with ammonia, followed by chloroform extraction, gave a crude product (40 mg),shown by tic to contain only nuciferine (1) and nornuciferine (3).Chromatography on neutral alumina gave 1 (25 mg) and 3(10 mg).The above experiment was repeated, with the modification that the A7-oxide S02 complex was refluxed not with acid, but with 5% aqueous sodium hydroxide. Preparative tic (2% MeOH in CHCls, A1203) gave I (38 mg), 3 (18 mg), and dehydronuciferine (12, 25 mg).
It is demonstrated that the ionization potentials of primary, secondary, and tertiary aliphatic amines correlate very well with the inductive and polar substituent constants, the only seriously deviating value being that for ammonia, itself. The correlation equation is found to be EI = 9.62 + 13.8 ΣσI.
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