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Phthalan is used in the synthesis of nine-membered cyclic dione ethers. It is used along with excess Li metal in the presence of 4,4'-Di-tert-butylbiphenyl, B21470, results in opening of the furan ring. It is used in the synthesis of functionalized benzylic alcohols.
Katsuhiko Tomooka; Lan-Fang Wang; Fumiaki Okazaki; Takeshi Nakai. External chiral ligand-induced enantioselective lithiation/SE2 reactions of isochroman and phthalan. Tetrahedron Letters. 2000, 41 6121-6125.
Bondoc E.; Sakurai S.; Morris K.; Chiang WY.; Laane J. Fluorescence and electronic absorption spectra of phthalan: Two-dimensional vibrational potential energy surface for the ring-puckering and flapping in the S-1(pi,pi(*)) state. Journal of Chemical Physics. 2000, 112 (15), 6700-6706.
For use in synthesis of nine-membered cyclic dione ethers, see: Synlett, 909 (1993).
Treatment of phthalan with excess Li metal in the presence of 4,4'-Di-tert-butylbiphenyl, B21470, results in opening of the furan ring. Sequential introduction of two different electrophiles can be effected in the resulting bis-benzylic species, consequently phthalan can be regarded as an o-xylene dianion synthon. This approach provides a convenient access to diols and hydroxy acids which can be readily dehydrated to benzo-fused 6- or 7-membered cyclic ethers or lactones: Tetrahedron, 51, 3351 (1995); see also: J. Org. Chem., 61, 4913 (1996); Tetrahedron Lett., 39, 7759 (1998).
Hazard Statements: H227
Precautionary Statements: P210-P280-P370+P378q-P501c
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