D,l-10-Camphorsulfonyl chloride

Calcium carbonate as support for palladium catalyst, 46, 90 Calcium hydride, 46, 58 D,L-Camphor, sulfonation to d,l-10-camphorsulfonic acid, 46,12 10-Camphorchlorosulfoxide, 46, 56 d,l-10-Camphorsulfonic acid, 46,12 conversion to acid chloride, 45,14 10-Camphorsulfonyl chloride, 45, 56 d,l-10-Camphorsulfonyl chloride,... 

Oxidation, of d,l 10-camphorsulfonyl chloride to d,l ketopime acid with potassium permanganate, 46, 55... 

D,L-10-Camphorsulfonyl chloride may be oxidized to ketopinic acid (p. 55). The optically active forms of the sulfonyl chloride are useful for resolving alcohols and amines into optical antipodes. 

Aq. K-permanganate and D,L-10-camphorsulfonyl chloride added alternately to vigorously stirred aq. Na-carbonate heated on a steam bath, and heating continued 1 hr. D,L-ketopinic acid. Y 38-43%. P. D. Bartlett and L. H. Knox, Org. Synth. 45,55 (1965). 

D,L-Ketopinic acid has been prepared by oxidation of bornyl chloride with nitric acid at 20° or with perbenzoic acid in acetic acid from 10,10-dinitrocamphan-2-on or apocamphan-2-ol-l-carboxylic acid with alkaline permanganate and from the oxidation of 10-camphorchlorosulfoxide, obtained from 10-camphorsulfonyl chloride by the action of pyridine, with potassium permanganate. The present procedure represents a simplification of the latter and gives as high an overall yield. ... 

Resolution 3t3-Acetoxy-A. etienic add. T-Acid from a tetranitrofluorenone and an optically active hydroxylamine. i><—>Butane-2,3-diol. L.(+)-Butane-2,3-dithiol. (By crystallization Silver acetate). 10-Camphorsulfonic acid. 10-Camphorsulfonyl chloride. 4-(4-Carboxy-phenyl) semicarbazide. Complex from ethylene, platinous chloride, and (- -)-l-phenyi-2-aminopropane. Debydroataetylamine. Diisopinocampheylborane. Di-p-toluoyl-o-tartrate. d- and /-u-Phenylethylamiiie. L-Pyrrolidonecarboxylic add. a-(2,4,S,7-Tetianitro-9-fluorenyl-ideneaminooxy)-propionic acids. 

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