Abstract
The structures of 8- and 9-iodocamphorquinone bis(ethylene ketal) have been confirmed by spectroscopic and single crystal X-ray analysis. The unexpected formation of the latter isomer is attributed to intramolecular rearrangement of the camphor skeleton, the mechanistic details of which have been explored using coset analysis.
References
1.
Sabbagh I.T.
, and
Kaye P.T.
, J. Molec. Structure: THEOCHEM , (submitted).
2.
Sabbagh I.T
, PhD thesis , Rhodes University , 2006 .
3.
Antkowiak R.
, and
Antkowiak W.Z.
, Pol. J. Chem. , 1994 , 68 , 2297 ; T. Money, Nat. Prod. Rep. , 1985, 2 , 253
4.
Cachia P.
,
Darby N.
,
Eck C.R.
, and
Money T.
, J. Chem. Soc., Perkin I , 1976 , 359 .
5.
Komarov I.V.
,
Monsees A.
,
Spannenberg A.
,
Baumann W.
,
Schmidt U.
,
Fischer C.
, and
Börner A.
, Eur. J. Org. Chem. , 2003 , 138 .
6.
Klein R.
, MSc thesis , Rhodes University , 1999 .
7.
Lobb K.A.
, unpublished work.
8.
Collins C.J.
, and
Johnson C.K.
, J. Am. Chem. Soc. , 1973 , 95 , 4766 ; C.J. Collins and C.K. Johnson, J. Am. Chem. Soc. , 1974, 96 , 2514.
9.
Otwinowski Z.
, and
Minor W.
, in Methods in Enzymology ,
Carter C.W.
, and
Sweet R.M.
(eds.), Academic Press , New York , 1997 , pp. 307 –326 .
10.
Sheldrick G.M.
, SADABS, Program for Empirical Absorption Correction of Area Detector Data ; University of Göttingen , Germany , 1996 .
11.SHELXS-86 :
Sheldrick G.M.
, in Crystallographic Computing 3 ,
Kruger G. M.
, and
Goddard R.
(eds.), Oxford University Press , Oxford, UK , 1985 , pp. 175 –178 .
12.
Sheldrick G.M.
, SHELXL-97, Program for refinement of crystal structures , University of Göttingen , Germany , 1997 .
