Trimethylsilyl cyanide (1) and N-(trimethylsilyl)diphenylmethyleneamine (2) reacted with α-aryl-N-phenyl-nitrones to afford the corresponding 1: 1 adducts 4 and 5 respectively. Thermal decomposition of 4 in refluxing xylene gave azoxybenzene, stereoisomers of 2,3-diarylsuccinonitriles, α-iminonitriles and/or benzanilides, whose yields depended on the nature of substituents on phenyl group of 4. On heating in benzene 5 afforded a mixture of azoxybenzene and meso-N,N′-bis(diphenylmethylene)-1,2-diarylethylenediamines. On the other hand, reactions of 1 and 2 with N-(diphenylmethylene)aniline N-oxide or N-(9-fluorenylidene)aniline N-oxide did not give the corresponding 1: 1 adducts, but instead compounds arising from thermal decomposition of initial 1: 1 adducts were directly obtained. The reaction of 1 with N-(p-diethylaminophenyl)-α-phenylnitrone leading to the corresponding α-imino nitrile is also described.
Stereoselective Syntheses of cis-and trans-Isomers of α-Hydroxyα,β-dibenzyl-γ-butyrolactone Lignans:New Syntheses of (±)-Trachelogenin and (±)-Guayadequiol.-A highly stereoselective electrophilic addition reaction to the metal enolates of the β-substituted α-benzyl-γ-butyrolactone derivatives such as (I) and (XI) is described. This method is applied to the syntheses of the title compound trachelogenin (X) and guayadequiol (XIV), examples of trans-and cis-isomers in the . alpha.hydroxy-α,β-dibenzyl-γ-butyrolactone lignan series.-(MORITANI, Y.; FUKUSHIMA, C.; UKITA, T.; MIYAGISHIMA, T.; OHMIZU, H.; IWASAKI, T.; J.
Die Acylaminomalonate (I) reagieren mit den Alkylhalogeniden (II) in guten Ausb. zu den Acylaminomalonsäuremonoestern (III), deren anodische Oxidation in Gegenwart der Alkohole (IV) über eine abnorme Kolbe‐Reaktion zu den α‐Alkoxy‐oz‐aminosäurederivaten (V) führt.
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Umsetzung entsprechender Azaheptafulvene (III) mit Sulfenen (IV) (in situ aus den Salzen (I) und den Sulfonylchloriden (II)) liefert die cis‐Addukte (Va), (Vb), die trans‐Addukte (Vc) (durch unmittelbare Epirnerisation der ebenfalls prim. gebildeten cis‐Isomeren) bzw. die cis‐Addukte (Vd)‐(Vf) (Diskussion des Reaktionsmechanismus).
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