J-Aromaticity

Pavlath, A E, Lefffler, A J Aromatic Fluorine Compounds Monograph... 

The rigidity of the hexacyclic cage structure of koumine (18) renders some of its chemical behavior quite unusual, for instance, the resistance to Hofmann degradation shown by /Va-acetyldihydrokoumine methyl hydroxide (27). However, owing to the presence of a /J-aromatic imino system in 18, reductive cleavage by sodium-alcohol to yield dihydrokouminol (39) proceeds smoothly. This reaction has been considered to occur through a radical-anion mechanism as indicated in Scheme 12 (27). 

Forrester, a. r., hay, j. m. and Thomson, r. h. Organic Chemistry of Stable Free Radicals (Academic Press, 1968). garratt, p. j. Aromaticity (McGraw-Hill, 1971). 

Pospisil, J. Aromatic and Heterocyclic Amines in Polymer Stabilization. Vol. 124, pp. 87-190. 

Garratt, P. J. Aromaticity. New York McGraw Hill 1971 88) Clar, E. The aromatic sextet. New York Wiley 1972... 

MILLER, J. Aromatic Nucleophilic Substitution (Elsevier, 1968). nonhebel, d. c. and walton, j. c. Free-radical Chemistry (CUP,... 

Gatratt, P. J. Aromaticity, J. Wiley, New Ycjrk, 1986 Loydk, D. Non-Benzenoid Conjugated Carboxcyclic Compounds-, Elseveir, Amsterdam, 1984. 

Pavlath, A.E. Leffler, A.J. Aromatic Fluorine Compounds, Reinhold New York, 1962. 

Pavlath, A E,Lefffler, A J Aromatic Fluorine Compounds Monograph No 155, American Chemical Society Washington, DC, 1962, pp 12-45... 

Steel, P. J., Aromatic Biheterocycles Syntheses, Structures, and Properties,... 

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