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Thursday, 15 May 2014

NMR EXAMPLE

<br /><br /> Reaction Scheme: <IMG src="/images/empty.gif">Deprotection of a tert-butyldimethylsilyl ether<IMG src="/images/empty.gif">


1H NMR (300 MHz; (CD3)2CO)
11.76 (1 H, s, OH (naph.) [exch]),
8.74 (1 H, dd, J 8.5 and 1.0, naph.),
8.10 (1 H, d, J 9.0, naph.),
7.89 (1 H, dd, J 8.5 and 1.5, naph.),
7.86 (1 H, dd, J 6.5 and 2.0, cyclop.),
7.59 (1 H, ddd, J 8.5, 7.0 and 1.5, naph.),
7.41 (1 H, ddd, J 8.5, 7.0 and 1.0, naph.),
7.22 (1 H, d, J 9.0, naph.),
6.50 (1 H, dd, J 6.5 and 2.0, cyclop.),
6.18 (1 H, q, J 2.0, cyclop.),
5.26 (1 H, d, J 5.5, OH (cyclop.) [exch]),
4.69 (1 H, dd, J 5.5 and 2.0, cyclop.)

Reference s
J. H. Clark, Chem. Rev., 1980, 80, 429 doi:10.1021/cr60327a004
E. J. Corey, A. Venkateswarlu, J. Am. Chem. Soc., 1972, 94, 6190 doi:10.1021/ja00772a043
A. B. Smith, III, G. R. Ott, J. Am. Chem. Soc., 1996, 118, 3095 (TBAF/AcOH)
K. C. Nicolaou, S. E. Webber, Synthesis, 1986, 453 (HF.py) doi:10.1055/s-1986-31673




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