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Isotopic scrambling in the reported synthesis of dehydro-2- norbornyl and 2-norbornyl derivatives labeled at C-3 with 14C

✍ Scribed by C. C. Lee; F. L. Kung

Publisher: John Wiley and Sons
Year: 1972
Tongue: French
Weight: 138 KB
Volume: 8
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2590080110

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✦ Synopsis

The r e c e n t l y r e p o r t e d s y n t h e a i s o f C-3 l a b e l e d dehydro-2-norbornyt and 2-norbornyt d e r i v a t i v e s ( 1 ) was found t o be i n e r r o r . Only about 7 0 % o f t h e " C -l a b e l was l o c a t e d a t C-3, t h e o t h e r 30% b e i n g found a t C-2. One o f t h e e t e p s i n t h e o r i g i n a l aynt h e s i s , i n v o l v i n g t h e c o n v e r s i o n of e t h y l e n e chlor o h y d r i n t o e t h y l e n e c y a n o h y d r i n , waa shown t o be r e s p o n s i b l e f o r t h i s i s o t o p i c s c r a m b l i n g .

The recently reported synthesis of a mixture of wand ~-3-l'C-dehydr0-2-norborneols(~) has been found to be i n error in that the "C-label was not solely located at C-3.

2-norbornanone, the original degradation was carried out by treatment with

CsHsMgBr to give 2-phenyl-w-2-norborneol followed by oxidation with KMnOI-KOH to give CbHsCOOH, the activlty i n this latter acid being a measure of the "C-content at C-2.(2) refluxing of the reaction mixture f o r 5 days(2) and this gave variable yields.

After hydrogenation and then oxidation to

The oxidation to CsHsCOOH involved the

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