3-aryl-3-hydroxy-2,2,4,4-tetramethylcyclobutanones and 1-aryl-2,2,4-trimethyl-1,3-pentadiones were prepared from arylation of 1,1,3,3-tetramethyl-5,8-dioxapiro [3,4]octan-2-one followed by hydrolysis using THF and HCl respectively.
RobertsJ.D., and GreenC., J. Am. Chem. Soc., 1946, 68, 214.
3.
NaikA.; FerroM., and WormanJ., Division of Organic Chemistry, 217th ACS National Meeting, Ananhein, CA., March 21~25, 1999, No. 198.
4.
HasekR.H., ClarkR. D., ElamE. V., and NationsR. G., J. Org. Chem., 1962, 27, 3106; E.A. LaLancette, J. Org. Chem., 1964, 29, 2957; L.A. Weintraub, D.L. Wilson and D.P. Hollis, J. Am. Chem. Soc., 1964, 86, 4880; J. Org. Chem., 1965, 30, 1805; E.R. Cullen, F.S. Guziec and C.J. Murphy, 1982, 47, 3563; Y. Apeloig, I. Zharv, D. Bravo-Zhivotovskii, Y. Ovechinnikov and Y. Struckov, J. Organomet. Chem., 1995, 499, 73; H. Giera and R. Huisgen, Liebigs Ann. Recl., 1997, 8, 1685.
5.
An exceptional example is reaction of the titled compounds with cyclopentadienyl magnesium bromide, see JacobsS.J., ShultzD. A., JainR., NovakJ., and DoughertyD. A., J. Am. Chem. Soc., 1993, 115, 1744.
6.
LinW.C., and CannonG. W., J. Chin, Chem. Soc., 1989, 36, 371; Chem. Abstr., 1989, 109, 157711m.
7.
FadelA., YefsahR., and SalauenJ., Synthesis, 1987, 37.
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ShurvellH.F., GordonR. D., HesterR. E., and GirlingR. B., Spectrochim. Acta, Part A, 1984, 40, 615.
9.
RobertsJ.D., and MorelandW. T., Jr., J. Am. Chem. Soc., 1953, 75, 2167.
