Quinones Perkin reaction

Nakatsubo F, Higuchi T (1975) Synthesis of 1,2-diarylpropane 1,3 diols and determination of their configurations Holzforschung 29 193-198 Ralph J, Ede RM, Robinson NP, Main L (1987) Reactions of /f-aryl lignin model quinone methides with anthrahydroquinone and antranol J Wood Chem Technol 7 133 160 Ralph J, Young RA (1983) Stereochemical aspects of lignin model (S aryl ether quinone methide reactions J Wood Chem Technol 3 161-182 Sarkanen KV, Wallis AFA (1973) Oxidative dimerizations of (E)- and (Z) isoeugenol (2 methoxy-4-propenylphenol) and (E) and (Z)-2,6-dimethoxy-4-propenylphenol JCS Perkin I 1973 1869-1878... 

Analogous results were reported earlier concerning the Perkin reaction of quinones. Treatment of 2,6-dimethoxy-p-benzoquinone with propionic anhydride in the presence of sodium propionate affords a mixture of condensation-derived products (12) and (13) (Scheme 6). However, when the reaction is carried out under milder conditions, among the products isolated is the 3 lactone (14). Compound (14) can be converted under Perkin conditions to (12) and (13). It is noted that (14) could be in equilibrium with dimethoxybenzoquinone and methylketene its isolation does not prove with certainty its intermediacy in the formation of (12) and (13). Thus, the actual mechanism of this condensation is not necessarily as simple as indicated in Scheme 2 and may involve more than one distinct pathway, depending on the exact nature of the particular substrate or base employed. 

Leary, G. Miller, I. J. Thomas, W. Woolbouse, A. D. The chemistry of reactive lignin intermediates. Part 5. Rates of reactions of quinone methides with water, alcohols, and carboxylic acids. J. Chem. Soc., Perkin Trans. 1977, 2, 1737-1739. 

Schuchmann MN, Bothe E, von Sonntag J, von Sonntag C(1998) Reaction of OH radicals with benzo-quinone in aqueous solutions. A pulse radiolysis study. J Chem Soc Perkin Trans 2 791-796 Schuchmann MN, Schuchmann H-P, Knolle W, von Sonntag J, Naumov S, Wang W-F, von Sonntag C (2000) Free-radical chemistry of thiourea in aqueous solution, induced by OH radical, H atom, cx-hydroxyalkyl radicals, photoexcited maleimide.and the solvated electron. Nukleonika 45 55-62... 

The quinone methide (11) derived from flavan by a retro-Diels-Alder reaction gives only a 4% yield of acridine when heated with aniline. However, the other products include the diphenylmethane (12) and the Mannich base (13) both of which yield the tricyclic compound upon pyrolysis (J.L. Asherson. 0. Bilgic and D.W. Young, J. chem. Soc. Perkin I, 1980, 522). 

Arisawa, M., Ramesh, N.G., Nakajima, M., Tohma, H., and Kita, Y, Hypervalent iodine(lll)-induced intramolecular cychzation of a-(aryl)alkyl-P-dicarbonyl compounds a convenient synthesis of benzarmulated and spirobenzannulated compounds, /. Org. Chem., 66, 59, 2001. Eberson, L., Reaction between organic and metal ion species, in Electron Transfer Reactions in Organic Chemistry, Reactivity and Structure, Vol. 25, Hafner, K., Lehn, J.-M., Rees, C.W., von Rague-Schleyer, R, Trost, B.M., and Zahradnik, R, Eds., Springer-Verlag, Berhn, 1987, chap. 7. Bockman, T.M., ShuMa, D., and Kochi, J.K., Photoinduced electron transfer from enol silyl ethers to quinone. Part 1. Pronounced effects of solvent polarity and added salt on the formation of a-enones, J. Chem. Soc., Perkin Trans. 2, 1623, 1996. 

---