Homophthalic acid (1) and arylcarboxyaldehydes were condensed to form 4-arylideneisochroman-1,3-dione (3) in acetic anhydride in the presence of ammonium acetate under focused microwave irradiation. The stereochemistry of the products was determined by NMR and by X-ray diffraction of one isomer.
BarryR.D., Chem. Rev., 1964, 12, 229; K. Nozawa, M. Yamada, Y. Tsuda, K. Kawai and S. Nakajima, Chem. Pharm. Bull., 1981, 29, 3486; R. Okunaka, T. Honda., M. Kondo, Y. Tamura and Y. Kita, Chem. Pharm. Bull., 1991, 39, 1298.
2.
VilleminD., LabiadB., and LoupyA., Synth. Commun., 1993, 23, 419.
3.
JonesG., Chem. Rev., 1967, 15, 204.
4.
HayesB.L., Microwave Synthesis-Chemistry at the Speed of Light, CEM publishing, Matthews2002.
5.
Buu-HoïM., Comp. Rend., 1940, 211, 330.
6.
JonesJ.B., and PindersA. R., J. Chem. Soc., 1958, 2612.
7.
GuirguisN.R., AwadB. N., and HefniH. A., J. Prakt. Chem., 1990, 332, 425
8.
ShawR., RoaneD., and NeddS., J. Chem. Educ., 2002, 79, 67 and references cited.
9.
We have described thermochromic ethylenes: VilleminD., HachémiM., and HammadiM., J. Chem. Res (S), 2003, under press.
10.
SheldrickG.M., Acta Cryst, 1990, A46, 467; G. M. Sheldrick, 1997, SHELX97. Program for the Refinement of Crystal Structures, University of Gottingen, Germany.