A facile method for deprotection of O-allylphenols

Chemical and Pharmaceutical Bulletin

Volumn 51, Issue 10, 2003, Pages 1220-1221

  Yamada, Makoto ^a   Watanabe, Shin Ichi ^a   Hoshino, Osamu ^a   Ishizaki, Miyuki ^a   Hayashida, Maiko ^a   Tanaka, Atsuko ^a   Hara, Hiroshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Allyl aryl ethers; Deprotection; Palladium on carbon

Indexed keywords

ALKYLPHENOL; CARBON; PALLADIUM; ALLYL COMPOUND; PHENOL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; DEBROMINATION; DEPROTECTION REACTION; DRUG SYNTHESIS; ROOM TEMPERATURE; CHEMISTRY; METHODOLOGY;

ALLYL COMPOUNDS; CHEMISTRY, PHARMACEUTICAL; PHENOLS;

EID: 2442509936     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.51.1220     Document Type: Article

References (17)

1. Green T. W., Wuts P. M. G., "Protecting Groups in Organic Synthesis," 3rd ed., John Wiley & Sons, New York, 1999.
2. Beugelmans R., Bourdet S., Bigot A., Zhu J., Tetrahedron Lett., 35, 4349-4350 (1994).
3. Bois-Choussy M., Neuville L., Beugelmans R., Zhu J., J. Org. Chem., 61, 9309-9322 (1996).
4. Four P., Guibe F., Tetrahedron Lett., 23, 1825-1828 (1982).
5. Dessolin M., Guillerez M.-G., Thieriet N., Guibe F., Loffet A., Tetrahedron Lett., 36, 5741-5744 (1995).
6. Eicher T., Ott M., Speicher A., Synthesis, 1996, 755-762 (1996).
7. Chandrasekhar S., Reddy C. R., Rao R. J., Tetrahedron, 57, 3435-3438 (2001).
8. Honda M., Morita H., Nagakura I., J. Org. Chem., 62, 8932-8936 (1997).
9. Franco D., Panyella D., Rocamora M., Gomez M., Clinet J. C., Muller G., Dunach E., Tetrahedron Lett., 40, 5685-5688 (1999).
10. Yasuhara A., Kasano A., Sakamoto T., J. Org. Chem., 64, 4211-4213 (1999).
11. Boss R., Scheffold R., Angew. Chem., Int. Ed., 15, 558-559 (1976).
12. Hara H., Watanabe S., Yamada M., Hoshino O., J. Chem. Soc., Perkin Trans. 1, 1996, 741-746 (1996).
13. lH-NMR spectroscopy and high resolution mass spectrometry.
14. Ten percent Pd/C was purchased from Kojima Chemical Co. Ltd.
15. Tetraphenol 2b could not be extracted into organic solvent because of its high polarity. Structure of 2b was determined as the corresponding tetraacetate 2e.
16. Similar isomerization of allyl ether to enol ether was reported using Pd/C in boiling benzene; Carless H. A. J., Haywood D. J., J. Chem. Soc. Chem. Commun., 1980, 980-981 (1980).
17. lH-NMR spectroscopy and behavior on thin layer chromatography.