Perkin reaction and related reactions

The Perkin Reaction and Related Reactions John R. Johnson... 

For a review of the discovery of the Perkin condensation and related reactions, see J. R. Johnson, Org. React., 1942, 1, 210. The reader is also referred to this review for more detailed discussions of the work as well as a greater number of examples published in this area prior to ca. 1940. 

For a review of these and related reactions, see Abramovitch Barton Find Tetrahedron 1988, 44. 3039-3071. l, Barton Blazejewski Charpiot Find Motherwell Papoula Stanforth J. Chem. Soc.. Perkin Tram. 1 1985, 2667 O Donnell Bennett Jacobsen Ma Tetrahedron Lett. 1989, 30. 3913. 

Theruvathu JA, Flyunt R, AravindakumarCT, von Sonntag C (2001a) Rate constants in the reactions of ozone with DNA, its constituents and related compounds. J Chem Soc Perkin Trans 2 269-274 Theruvathu JA, AravindakumarCT, Flyunt R, von Sonntag C (2001b) Fenton chemistry of 1,3-dimeth-yluracil. J Am Chem Soc 123 9007-9014... 

Thomas JK (1967) Pulse radiolysis of aqueous solutions of methyl iodide and methyl bromide. The reactions of iodine atoms and methyl radicals in water. J Phys Chem 71 1919-1925 Tsang W, Hampson RF (1986) Chemical kinetic data base for combustion chemistry, part I. Methane and related compounds. J Phys Chem Ref Data 15 1086-1279 UlanskiP, von Sonntag C (1999) The OFI-radical-induced chain reactions of methanol with hydrogen peroxide and with peroxodisulfate. J Chem Soc Perkin Trans 2 165-168 Ulanski P, Bothe E, Hildenbrand K, von Sonntag C, Rosiak JM (1997) The influence of repulsive electrostatic forces on the lifetimes of polyfacrylic acid) radicals in aqueous solution. Nukleonika 42 425-436... 

Furimsky E, Howard JA, Selwyn J (1980) Absolute rate constants for hydrocarbon autoxidation. 28. A low temperature kinetic electron spin resonance study of the self- reactions of isopropylperoxy and related secondary alkylperoxy radicals in solution. Can J Chem 58 677-680 Gebicki JM, Allen AO (1969) Relationship between critical micelle concentration and rate of radiolysis of aqueous sodium linolenate. J Phys Chem 73 2443-2445 Gebicki JM, Bielski BHJ (1981) Comparison of the capacities of the perhydroxyl and the superoxide radicals to initiate chain oxidation of linoleic acid. J Am Chem Soc 103 7020-7022 Gilbert BC, Holmes RGG, Laue HAH, Norman ROC (1976) Electron spin resonance studies, part L. Reactions of alkoxyl radicals generated from alkylhydroperoxidesand titanium(lll) ion in aqueous solution. J Chem Soc Perkin Trans 2 1047-1052... 

Beagley, B. Betts, M. J. Pritchard, R. G. Schofield, A. Stoodley, R. J. Vohra, S. Hidden axial chirality as a stereodirecting element in reactions involving enol(ate) intermediates. Part 1. Cyclization reactions of methyl (4R)-3-(2-diazo-3-oxobutanoyl)thiazolidine-4-carboxyl-ate and related compounds. J. Chem. Soc. Perkin Trans. 1 1993, 1761-1770. 

A. P. Glaze, S. A. Harris, H. G. Heller, W. Johncock, S. N. Oliver, P. J. Strydom, and J. Whittall, Photochromic heterocyclic fulgides. Part 4.1. The thermal and photochromic reactions of (E)-isopropylidene-[a-(2-and-(3-thienyl ethylidene] succinic anhydrides and related compounds, J. Chem. Soc., Perkin. Trans. 1, 1985, 958-961. 

Schiesser, C. H., Styles, M. L. On the radical Brook and related reactions an ab initio study of some (1,2)-silyl, germyl and stannyl translocations. J. Chem. Soc., Perkin Trans. 2 1997, 2335-2340. 

Bossio, R., Marcaccini, S., Pepino, R., Torroba, T. Studies on isocyanides and related compounds synthesis of benzojcjthiophenes by way of acid-induced three-component reactions. J. Chem. Soc., Perkin Trans. 1 1996, 229-230. 

It is interesting that in one case, at least, a condensation related to the Perkin reaction has been stopped at the aldol, stage. When a mixture of benzaldehyde and ethyl acetate was added to an ether solution of sodium triphenyl methyl and the reaction mixture was worked up after one minute, a 26 per cent yield of the aldol (V) was obtained.13 When the reaction was carried out over a longer period of time, ethyl cinnamate was formed.14... 

For the use of indium catalyzed reactions in organic synthesis, see (a) Chauhan, K.K. Frost, C.G. J. Chem. Soc., Perkin Trans. 1, 2000, 3015. For a list of reagents used in this type of reaction, see (b) Smith, M.B. March, J. March s Advanced Organic Chemistry, 5th ed. Wiley New York, 2001, pp 1205-1211. (c) For reactions of this type, see Reference 26, pp 1126-1133. Also see (d) Blomberg, C. Reactions and Structure. Concepts in Organic Chemistry, Vol. 31. The Barbier Reaction and Related One-Step Processes, Springer Verlag, Berlin, 1993. 

This reaction is related to the Perkin Reaction and Pechmann Reaction. 

Gilbert BC, King DM, Thomas CB (1981) Radical reactions of carbohydrates. Part 2. An electron spin resonance study of the oxidation of D-glucose and related compounds with the hydroxyl radical. J Chem Soc Perkin Trans 2 1186-1199... 

Lanosteryl S-methyl dithiocarbonate in xylene added during 0.5 hr. under argon to a stirred and refluxing mixture of tributylstannane and xylene, and refluxing continued 2 hrs. -> lanosta-8,24-diene. Y 83%. - This reduction is part of a method for the deoxygenation of sec. alcohols. F. e. and related reactions s. D. H. R. Barton and S. W. McCombie, Soc. Perkin I 1975, 1574. 

Reviews P. E. Spoerri, A. S. DuBois, Org. React. 5, 387 (1949) Thomas, Anhydrous Aluminum Chloride in Organic Chemistry (New York, 1941) p 504 W. Ruske in Friedel-Crafts and Related Reactions vol. Ill, Part 1, G. A. Olah, Ed. (Interscience, New York, 1964) p 383 M. I. Amer et al, J. Chem. Soc. Perkin Trans. 11983,1075 V. V. Arkhipov etal, Chem. Heterocycl. Compd. 33, 515 (1997) R. Kawecki et ah, Synthesis 1999,751. Cf. Gatterman Aldehyde Synthesis Houben-Fischer Synthesis. 

Bowman RM, Collins JF, Grundon MF (1973) Quinoline alkaloids. Part XIV. Asymmetric synthesis by the peroxy-acid-oleiin reaction. The absolute stereochemistry of balfourodine, isobalfourodine, and related compounds, and the biosynthesis of isomeric dihydrofuro- and dihydropyrano-derivatives. J Chem Soc Perkin Trans 1 626-632... 

Brooke GM Ferguson JAKJ (1986) Partially fluorinated heterocyclic compounds. Part 22. The preparation of allyl 2,5,6-trifluoropyrimidin-4-yl ether and related compounds and a study of their Claisen rearrangement reactions. A new route to 5-fluorouracil and barbituric acid derivatives. J Chem Soc Perkin Trans 1 515-520... 

Danswan GW, Hairsine PW, Rowlands DA, Taylor JB, Westwood R (1982) Synthesis and reactions of some novel imidazobenzoxazines and related systems. J Chem Soc, Perkin Trans 1 1049-1058. doi 10.1039/P19820001049... 

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