Lewis or Bronsted acid provoked rearrangements in ortho-(1,1-dimethylpropenyl)phenols

Tetrahedron

Volumn 53, Issue 15, 1997, Pages 5573-5580

  Nielsen, Simon Feldbæk ^a,b   Olsen, Carl Erik ^c   Christensen, Søren Brøgger ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b STATENS SERUM INSTITUT   (Denmark)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030892144     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00212-3     Document Type: Article

References (23)

1. (a) Balasubramanian, K.; Rajagopalan, K. Phytochemistry 1988, 27, 1552-1554.
2. (b) Burkhardt, G.; Schild, W.; Becker, H.; Grubert, M. Phytochemistry 1992, 31, 543-548.
3. (c) Monache, F. D.; Botta, B.; Nicoletti, M.; Coêlho, J. S. B.; Lyra, F. D. A. J. Chem. Soc., Perkin 1 1981, 484-488.
4. McCabe, P. H.; McCrindle, R.; Murray, R. D. H. J. Chem. Soc. (C) 1967, 145-151.
5. (a) Ballantyne, M. M.; McCabe, P. H.; Murray, R. D. H. Tetrahedron, 1971, 27, 871-877.
6. (b) Ito, C.; Fujiwara, K.; Kajita, M.; Ju-Ichi, M.; Takemura, Y.; Suzuki, Y.; Tanaka, K.; Omura, M.; Furukawa, H. Chem. Pharm. Bull. 1991, 39, 2509-2513.
7. (c) Zeng, L.; Zhang, R.-Y.; Meng, T.; Lou, Z.-C. J. Chrom. 1990, 513, 247-254.
8. (a) Murakami, T.; Hagiwara, M.; Tanaka, K.; Chen, C.-M. Chem. Pharm. Bull. 1973, 21, 1851-1852.
9. (b) Malhotra, S.; Sharma, V. K.; Parmar, V. S. J. Nat. Prod. 1988, 51, 578-581.
10. (c) Herz, W.; Bruno, M. Phytochemistry 1987, 26, 1175-1180.
11. Barton, D. H. R.; Bhati, A.; Mayo, P.; Morrison, G. A. J. Chem. Soc. 1958, 4393-4398.
12. Okely, H., M.; Grundon, M. F. J. Chem. Soc. Perkin 1, 1981, 897-899.
13. Molyneux, R. J.; Jurd, L. Tetrahedron 1970, 26, 4743-4751.
14. Nielsen, S. F.; Kharazmi, A.; Theander, T. G.; Christensen, S. B. In preparation.
15. Miller, B. J. Am. Chem. Soc. 1969, 91, 2170-2172.
16. Miller, B. J. Am. Chem. Soc. 1970, 92, 6246-6252.
17. (a) Lutz, R. P. Chem. Rev. 1984, 84, 205-247.
18. (b) Widmer, U.; Zsindely, J.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta. 1973, 56, 75-105.
19. Olah, G. A.; Spear, R. J.; Forsyth, D. A. J. Am. Chem. Soc. 1976, 98, 6284-6289.
20. (a) Marvell, E. N.; Anderson, D. R.; Ong, J. J.Org. Chem. 1962, 27, 1109-1110.
21. (b) Marvell, E. N.; Schatz, B. Tetrahedron lett. 1967, 67-70.
22. (c) Scheinmann, F.; Barner, R.; Schmid, H. Helv. Chim. Acta. 1968, 51, 1603-1608.
23. Synthesized as described in: Khan, S. A.; Krishnamurti, M. Ind. J. Chem 1983, 22B, 276-277.