Cesium fluoride-mediated claisen rearrangements of phenyl propargyl ethers: Substituent effects of an orthoalkoxy group on the benzene ring or modified propargyl residues

Heterocycles

Volumn 45, Issue 11, 1997, Pages 2261-2272

  Ishikawa, Tsutomu ^a   Mizutani, Akiko ^a   Miwa, Chizue ^a   Oku, Yumie ^a   Komano, Naoko ^a   Takami, Atsuya ^a   Watanabe, Toshiko ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001286507     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-97-7946     Document Type: Article

References (5)

1. H. Ishii, T. Ishikawa, S. Takeda, S. Ueki, and M. Suzuki, Chem. Pharm. Bull., 1992, 40, 1148.
2. T. Ishikawa, K. Nagai, N. Ohkubo, and H. Ishii, Heterocycles, 1994, 39, 371.
3. Monobenzoylation of catechol followed by isopropylation and hydrolysis resulted in ineffective preparation (overall yield: 9.9%) of o-isopropoxyphenol.
4. M. Harfenist and E. Thom, J. Org. Chem., 1972, 37, 841. The presence of the preferred conformation A in solution was supported by the NMR data of the propargyl ethers (13) of methyl vanillate described later. The 6-H of the primary propargyl ether (13b) appears at δ 7.05, while that of the tertiary propargyl ether (13 a) at δ 7.51 by anisotropy effect of the triple bond in the bulky propargyl residue.
5. M. F. Grundon, Tetrahedron, 1978, 34, 143.