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Planar chiral systems, IV. An efficient route for the preparation of 5‐formyl‐4‐hydroxy[2.2]paracyclophane (FHPC)
Author(s) -
Hopf Henning,
Barrett David G.
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199519950259
Subject(s) - chemistry , metalation , butyllithium , trimethylsilyl chloride , derivative (finance) , trimethylsilyl , cyclophane , yield (engineering) , dimethylformamide , phenol , phenyllithium , medicinal chemistry , organic chemistry , catalysis , molecule , materials science , solvent , financial economics , economics , metallurgy
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.