ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The stereochemical outcomes [ratios (1 R, 2 R, 4 R)-isoborneol/(l R, 2 S, 4 R) isborneol or (1R, 2 S, 4 S)-isoborneol(l S, 2 R, 4 S)-borneol and (1 RS, 2 RS, 4 RS)-isoborneol/(l RS, 2 SR, 4 RS)-borneol] in lithium, sodium and potassium/ammonia reductions without a proton source of the enantiomeric [(1 R, 4 R) or (1 S, 4 S)] and racemic (1RS, 4RS) forms of camphor under the same conditions differ strongly. This explains contradictory reports in the literature and, in the case of the reductions with potassium in which pinacol coupling does not compete, proves that the reductions involve bimolecular reactions between two ketyls, or between the ketone and the ketyl or the ketone dianion.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19820650143
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