Synthesis and Photochemical Transformations of a few 3,3-Bis(4-chlorophenyl)-5-aryl-2(3H)-furanones

Vidya Raman, Rakesh Natarajan, Tomson Devassia, Ligi M. Lalu

Abstract


A few 3,3-bis(4-chlorophenyl)-5-aryl-2(3H)-furanones were synthesized and their photochemical transformations were studied.  On direct irradiation, these aryl substituted 2(3H)-furanones underwent decarbonylation to yield corresponding a,b-unsaturated carbonyl compounds and upon sensitized irradiation, they underwent dimerization arising through a [2+2] cycloaddition reaction.


Keywords


4,4’-Dichlorobenzil, 2(3H)-furanones, 2(5H)-furanones, [2+2] cycloaddition.

Full Text:

PDF

References


Rappai JP, Raman V, Unnikrishnan PA et al. Preliminary investigations on the synthesis and antitumor activity of 3(2H)-furanones. Bioorg Med Chem Lett 2009; 19: 764–65.

Collins I. Saturated and unsaturated lactones. J Chem Soc Perkin Trans 1999; I: 1377-96.

Sun L, Vasilevich NI, Fuselier JA et al. Abilities of 3,4-diarylfuran-2-one analogs of combretastatin A-4 to inhibit both proliferation of tumor cell lines and growth of relevant tumors in nude mice. Anticancer Res 2004; 24: 179– 86.

Pratapan S, Ashok K, Cyr DR et al. Substituent effects in the photochemistry of 5-aryl-3,3-diphenyl-2(3H)-furanones. Steady-state and laser flash photolysis studies. J Org Chem 1988, 53, 5826-31.

Gopidas KR, Cyr DR, Das PK et al. Photochemical and thermal transformations of 3-benzyl-2(3H)-furanones and related substrates. J Org Chem 1987; 52: 5505-11.

Gopidas KR, Lohray BB, Rajadurai S et al. Sensitized photorearrangement of 3,3,5-triaryl-2(3H)-furanones to 3,4,5-triaryl-2(5H)-furanones. Steady-state and laser flash photolysis investigations. J Org Chem 1987; 52: 2831-38.

Davis HF, Lohray BB, Gopidas KR et al. Photoinduced electron-transfer reactions of 2(3H)-furanones and bis(benzofuranones). Spectral and kinetic behavior of radicals and radical cations. J Org Chem 1985; 50: 3685-92.

Lohray BB, Kumar CV, Das PK et al. Photochemical and thermal transformations of 2(3H)-furanones and bis(benzofuranones). A laser flash photolysis study. J Am Chem Soc 1984; 106: 7352-59.

Yogev A, Mazur Y. Irradiation of Enol Lactones. J Am Chem Soc1965; 87: 3520-21.

Krull IS, Arnold DR. The Hg senitized vapor phase photolysis of γ-crotonolactone and simple butenolides. Tetrahedron Lett 1969; 10: 1247-49.

Padwa A, Dehm D. Photochemical transformations of small ring carbonyl compounds. 68. Photochemical rearrangement in the 2(5H)-furanone system. J Am Chem Soc 1975; 97: 4779-81.

Padwa A, Brookhart T, Dehm D et al. Photochemical transformations of small ring carbonyl compounds. 101. Migratory aptitude studies in the photochemical rearrangement of 2(5H)-furanones. J Am Chem Soc 1978; 100: 8247-59.

Ohga K, Matsuo T. A study on the photochemistry of .ALPHA..BETA.-unsaturated .GAMMA.-lactones. III. Photodimerization of 2-penten-4-olide. Bull Chem Soc Jpn 1976; 49: 1590-94.

House HO, Ro RS. The Stereochemistry of Base-catalyzed Epoxidation. J Am Chem Soc1958; 80: 2428-33.

Payne GB, Williams PH. Reactions of Hydrogen Peroxide. VI. Alkaline Epoxidation of Acrylonitrile. J Org Chem 1961; 26: 651-59.

Buckles RE, Mock GV, Locatell L Jr. Toglic And Angelic Acids. Chem Rev 1955; 55: 659-77.

Ugai T, Tanaka S, Dokawa S. A new catalyst for acyloin condensation. J Pharm Soc Jpn 1943; 63: 269-300.

Breslow R. Mechanism of thiamine action: participation of a thiazolium zwitterion. Chem Ind (London) 1957; 893-94.

Breslow R. On the mechanism of thiamine action. IV. Evidence from studies on model systems. J Am Chem Soc 1958; 80: 3719-26.

Lapworth A. XCVI.—Reactions involving the addition of hydrogen cyanide to carbon compounds. J Chem Soc Trans 1903; 83: 995-1005.

Furniss SF, Hannaford AJ, Smith PWG et al. Vogel’s Textbook of Practical Organic Chemistry. ELBS. Fifth Edition, 1989: 1045.

Claisen L, Claparede A. Condensation of ketones with aldehydes. Ber 1881; 14: 2460-68.

Kuhn LP, Lutz RE, Bauer CR. A Spectroscopic Study of cis- and trans- Dibenzoylethylenes and Related Compounds. J Am Chem Soc 1950; 72: 5058-63.

Blatt AH. Pyrolyses of cis-phenyldibenzoylethylene, its oximes, and some related heterocyclic compounds. J Org Chem Soc 1950; 15: 869-72.

Blatt AH. Hydroxy Pyrrole Nitrones. II. J Am Chem Soc 1936; 58: 590-94.


Refbacks

  • There are currently no refbacks.