ISSN:
0749-1581
Keywords:
13C NMR
;
Tricyclo[3.2.1.02,4]octanes
;
Substituent effects
;
Geminal diphenyl
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 13C NMR chemical shifts for a series of exo- and endo-3,3-diphenyltricyclo[3.2.1.02,4]octanes are reported. Comparisons with the parent exo- and endo-tricyclo[3.2.1.02,4]octanes and with bicyclo[2.2.1]heptanes show that most of the chemical shifts are additive. Substituent effect constants are presented for the tricyclo[3.2.1.02,4]octyl system. Pronounced deshielding effects are seen in the endo series for C-6 and -7 of the alkene endo-3,3-diphenyltricyclo[3.2.1.02,4]oct-6-ene, the epoxide endo-3,3-diphenyltricyclo[3.2.1.02,4]octan-6,7-exo-oxide, and the tetracyclic exo-3,3-diphenyltetracyclo[3.3.1.02,406,8]nonane. The chemical shifts of C-3 and -8 are diagnostic for endo vs. exo substitution.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260270405
Permalink
