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NMR spin—spin decoupling studies of some 5,6-disubstituted bicyclo[2.2.2]oct-2-enes. Assignment of vinylic protons and demonstration of allylic coupling

✍ Scribed by David B. Roll; Bernard J. Nist; Alain C. Huitric


Publisher
John Wiley and Sons
Year
1967
Tongue
English
Weight
386 KB
Volume
56
Category
Article
ISSN
0022-3549

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✦ Synopsis


Assignment of the NMR signals of the vinylic protons has been accomplished by spin-spin decoupling in endo-S-nitro-exo-6-(p-chlorophenyl)-bicyclo[2.2.~]oct-~ene (I), endo-5-amino-exo-6-(p-chlorophenyI)-bicyclo[2.2.2]oct-2-ene hydrobromide (IV), endo-5-cyano-exo-6-(pp-chlorophenyl)-bicyclo[2.2.2]oct-2-ene (V), endo-5-cyano-endo-6-(p-chlorophenyl)-bicyclo[2.2.2]oct-2-ene (VII), all of which show significant differences in the chemical shifts of the two vinylic protons. A long-range coupling of 1.5 C.P.S. is demonstrated between H-1 and H-3 and between H-4 and H-2 in these systems.


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