The interaction of homophthalic anhydride with (triphenylphosphoranylidene)acetates


  • Oleh Valentinovich Shablykin Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine
  • Daniil Merzhyievsky
  • Olga Shablykina



homophthalic anhydride, (triphenylphosphoranylidene)acetates, Wittig reaction, self-condensation of homophthalic anhydride


In the study of the interaction of homo­phthalic anhydride and methyl (triphenyl­phosphoranylidene)­acetate, along with (1-oxo-1H-isochromen-3‑yl)acetate obtaining, two minor products – (1,3-dioxo-1,2,3,4-tetrahydronaphthalene-2-yl)acetate and 2‑((1‑oxo-1H-isochromen-3-yl)methyl)benzoic acid – had been isolated. The action of tert‑butyl (triphenyl­phosphoranylidene)­acetate on homo­phthalic anhydride didn’t lead to Wittig reaction; the encumbered ylide demonstrated only its basicity, and products of homo­phthalic anhydride self-condensation – 2‑((1‑oxo-1H-isochromen-3-yl)methyl)-benzoic acid and 12-hydroxy-5H-dibenzo[c,g]chromen-5-one – were formed.

Author Biography

Oleh Valentinovich Shablykin, Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine

Phd, senior reasercher


Kolodiazhnyi OI. Phosphorus Ylides; Chemistry and Application in Organic Synthesis by Oleg I Kolodiazhnyi. Wiley-VCH: Weinheim, 1999. 555 pp. ISBN 3-527-29531-3. DM 248.. Organic Process Research & Development 1999;3(5):380-380.

Abell A, Doyle I, Massy-Westropp R. The Wittig reaction with glutaric and succinic anhydrides. Australian Journal of Chemistry 1982;35(11):2277.

Kayser M, Hatt K, Hooper D. Mechanism of Wittig reaction with cyclic anhydrides. Canadian Journal of Chemistry 1992;70(7):1985-1996.

Abell A, Massy-Westropp R. Aspects of the mechanism of the Wittig reaction between cyclic anhydrides and stabilized phosphoranes. Australian Journal of Chemistry 1982;35(10):2077.

Aknin J, Molho D. Synthèse de la (carboxy-2' benzyl)-3 isocoumarine et de la spiro-3,3' phtalide dihydro isocoumarine. Bull. Soc. Chim. France, 1965;(10):3021-3024.

Bogdanov M, Mitrev Y, Tiritiris I. New Highly Diastereoselective Perkin/Michael Addition Domino Reaction between Homophthalic Anhydride and Aromatic Aldehydes: A Facile Approach to Blue-Fluorescent Dibenzo[c,h]chromenones. European Journal of Organic Chemistry 2010;2011(2):377-384.

Ishchenko V, Voevoda N, Shablykina O, Turov A, Khilya V. Reduction of 3-(carboxyaryl)isocoumarins with sodium borohydride. Chemistry of Heterocyclic Compounds 2012;47(10):1212-1224.

Jagtap P, Baloglu E, Southan G, Williams W, Roy A, Nivorozhkin A, Landrau N, Desisto K, Salzman A, Szabó C. Facile and Convenient Syntheses of 6,11-Dihydro-5H-indeno[1,2-c]isoquinolin- 5-ones and 6,11-Dihydro-5H-indolo[3,2-c]isoquinolin-5-one. Organic Letters 2005;7(9):1753-1756.

Sorrie A, Thomson R. Hydroxybenzotropones. Part III. Synthesis of a hydroxy-dimethoxydibenzotropone. Journal of the Chemical Society (Resumed) 1955;:2244.

Brockway A, González-López M, Fettinger J, Shaw J. Direct Displacement of Alkoxy Groups of Vinylogous Esters by Grignard Reagents. The Journal of Organic Chemistry 2011;76(9):3515-3518.

Shablykina О, Ishchenko V, Chumachenko S, Khilya V. Intramolecular cyclization of 3-(2-carboxyphenyl)- and 3 (2 carboxybenzyl)¬iso-coumarine. Taras Shevchenko Nat. Univ. Kyiv: Chem. Bull. 2013;49(1):64-66 (in Ukrainian).

Belgaonkar VH, Usgaonkar RN. Isocoumarins. Part XIV. Synthesis of 3-Benzyl-isocoumarins and 3-Benzyl-1(2H)isoquinolones. Indian J. Chem. 1975;13:336-338.