Novel oxidative nitrogen to carbon rearrangement found in the conversion of anilines to benzaldoximes by treating with HCHO/H2O2

Deprotonation with strong bases of N-vinyl ureas carrying an N′-aryl substituent leads to migration of the N′-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents α to the urea N atom may migrate from C to N.

Carbon atom

10.1039/c2cc38704b

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Citations (16)

ChemInform Abstract: BASIC TETRAHYDRODIBENZOFURAN DERIVATIVES WITH A 3-CARBON CHAIN BETWEEN NITROGEN AND THE QUATERNARY CARBON ATOM

Chemischer Informationsdienst (1979)

Wilhelm Fleischhacker M. KOEHL

Abstract Die NaBH 4 ‐Reduktion von Pummerers Keton (I) liefert ein 15:1‐Gemisch der epimeren Alkohole (IIa) und (IIb), die beim Behandeln mit Dimethylacetamid‐dimethylacetal unter Claisen‐Umlagerung stereospezifisch in die Säureamide (IIIa) (nicht rein isoliert) bzw. (IIIb) übergeführt (O I werden.

Nitrogen atom

Carbon atom

Quaternary carbon

Carbon fibers

Carbon chain

10.1002/chin.197904177

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Structure-activity relationship of cyclic imide herbicides. I. N-Substituted phenyl-3,4,5,6-tetrahydrophthalimides and related compounds.

Agricultural and Biological Chemistry (1976)

Hiroki Ohta Seiichi Suzuki H. Watanabe Tetsuo Jikihara Kuni Matsuya

In the course of the development of new herbicide (MK-616: N-(p-chlorophenyl)-3, 4, 5, 6-tetrahydrophthalimide), the structure-activity relationship of cyclic imide herbicides was investigated. Sixty N-substituted phenyl-3, 4, 5, 6-tetrahydrophthalimides and related compounds were prepared and their herbicidal activity were examined. The results indicate that, for high inhibitory activity, lipophilic tetramethylene moiety, double bond or nitrogen atom (s) in bridgehead position and N-(p-substituted) phenyl moiety are essential in these cyclic imides. New 4-(p-chlorophenyl)-1, 2-tetramethyleneurazole and 3 (p-chlorophenyl)-1, 5-tetramethylenehydantoin were found to be herbicidally active.

Moiety

Imide

Nitrogen atom

10.1271/bbb1961.40.745

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Citations (10)

Synthesis of cryptands with one carbon and one nitrogen bridgehead atom

Tetrahedron Letters (1985)

Byungki Son Czech P. Bronislaw Richard A. Bartsch

Cryptand

Nitrogen atom

Carbon atom