Anthrone (1) can be alkylated selectively to give O-, C,O- or C,C-substituted compounds 2, 4, or 5, respectively. Similarly, 5,5-dimethyl-3-isoxazolidinone (6) and 4-methylquinolone (9) yield N- or O-derivatives 7 and 8 or 10 and 11, respectively. The product ratios can be influenced strongly sometimes by use of different phase transfer catalysts, but the sensitivity of each reaction towards the catalysts is unique.
DehmlowE.V., KlauckR., J. Chem. Res. (S), 1994, 448–449.
5.
DehmlowE.V., KinniusJ., J. Prakt. Chem./Chem. Zeit., 1995, 337, 153–155.
6.
Survey: DehmlowE.V., chapter 9 (pp. 108–122) in Phase-Transfer Catalysis, Mechanisms and Syntheses, HalpernM., edit., ACS Symposium Series No. 659, American Chemical Society, Washington, D.C., 1997.
7.
DehmlowE.V., and DehmlowS. S., Phase Transfer Catalysis, 3rd Ed., VCH, Weinheim, 1993.
8.
StarksC., LiottaC., and HalpernM., Phase Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives, Chapman & Hall, New York, 1994.
9.
SassonY., and NeumannR., (edits.) Handbook of Phase Transfer Catalysis, Blackie Academic & Professional, London, 1997.
10.
WillnerI., and HalpernM., Synthesis, 1979, 177.
11.
MajumdarK.C., ChattopadhyayS. K., and KhanA. T., Synthesis, 1988, 552–553.
12.
LyB., DouH. J. M., HassanaliP., and VerducciJ., J. Heterocycl. Chem., 1977, 14, 1275–1277.
13.
Work by G. Thye.
14.
OliveJ.-L., PetrusC., and PetrusF., Bull. Soc. Chim. France, 1976, 1589–1594.
15.
FittonA.O., and SmalleyR. K., Practical Heterocyclic Chemistry, p. 59, Academic Press, London, New York, 1968.
16.
de Barry BarnettE., and MatthewsM. A., Ber., 1926, 59, 767–770
17.
MeyerK.H., IrschickA., and SchlösserH., Ber., 1914, 47, 1741–1755.
18.
HeymannH., and TrowbridgeL., J. Am. Chem. Soc., 1950, 72, 84–86.
19.
KaslowC.E., and CookD. J., J. Am. Chem. Soc., 1945, 67, 1969–1972.
20.
LottW.A., and ShawE., J. Am. Chem. Soc., 1949, 71, 70–73.
