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Planar chiral systems, IV. An efficient route for the preparation of 5-formyl-4-hydroxy[2.2]paracyclophane (FHPC)

✍ Scribed by Hopf, Henning ;Barrett, David G.

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 289 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199519950259

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✦ Synopsis

Abstract

For the preparation of the title compound, 4‐hydroxy[2.2]paracyclophane (1) is first converted to the carbamate 2. Metalation of 2 with sec‐butyllithium yields an ortho‐anion which after trapping with dimethylformamide and acidic work‐up provides 6 in 64% yield. Further application of the cyclophane anion include its capture by trimethylsilyl chloride to the trimethylsilyl derivative 3 (76%) and its Fries rearrangement to the phenol 4 (78%). The spectroscopic and analytical data of the new compounds are described in full detail.

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