The bromination of (−)-camphorquinone

作者: Desmond Cunningham , David H. Grayson , Patrick McArdle , John J. Walsh

DOI: 10.1016/S0957-4166(03)00090-9

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摘要: Abstract The reaction of (−)-camphorquinone with excess moist bromine gives (−)-(1S,5S)-1-bromomethyl-3,3-dibromo-8,8-dimethyl-7-oxabicyclo[3.2.1]octane-2,6-dione rather than 1-bromomethyl-3,5-dibromo-8,8-dimethyl-7-oxabicyclo[3.2.1]octane-2,6-dione as has been reported in the literature. controlled leads to (−)-(1S,5S)-3,3-dibromo-1,8,8-trimethyl-7-oxabicyclo[3.2.1]octane-2,6-dione and not 5-bromo-1-bromomethyl-8,8-dimethyl-7-oxabicyclo[3.2.1]octane-2,6-dione.

参考文章(7)
O. Manasse, E. Samuel, Reactionen des Campherohinons Berichte der deutschen chemischen Gesellschaft. ,vol. 30, pp. 3157- 3161 ,(1897) , 10.1002/CBER.189703003141
W. C. Evans, J. L. Simonsen, M. B. Bhagvat, 103. The bromination of camphorquinone Journal of The Chemical Society (resumed). pp. 444- 447 ,(1934) , 10.1039/JR9340000444
N. Walker, D. Stuart, An empirical method for correcting diffractometer data for absorption effects Acta Crystallographica Section A. ,vol. 39, pp. 158- 166 ,(1983) , 10.1107/S0108767383000252
G. M. Sheldrick, Phase annealing in SHELX-90: direct methods for larger structures Acta Crystallographica Section A Foundations of Crystallography. ,vol. 46, pp. 467- 473 ,(1990) , 10.1107/S0108767390000277
Melvin S. Newman, Concerning the Reduction of α-Bromoketones by Hydrogen Bromide Journal of the American Chemical Society. ,vol. 73, pp. 4993- 4994 ,(1951) , 10.1021/JA01154A533