ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Two CH3 groups at C(6) of 2-exo- (10a) and 2-endo-norbornyl p-toluenesulfonate 11a lower their solvolysis rates in 80% EtOH by factors of 28 and 16, respectively. A spirocyclopropyl group including C(6), as in 21a and 22a, reduces the rate of exo- and endo-ionization by factors of 250 and 8, respectively. The geminally dimethyl-substituted tosylates 10a and 11a yield the 2-exo-alcohol 10b, whereas the spirocyclopropyl-substituted tosylates 21a and 22a furnish rearranged 3-brendanol 23. These findings are readily rationalized by the inductive model, according to which norbornyl cation formation is controlled by the inductive effect of dorsal substituents.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19870700105
