ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reactions of 2exo- and 2endo-norbornyl bromide (1e and 2e, respectively) in 90% ethanol with a large excess of potassium hydroxide, and of 2exo-norbornyl p-toluenesulfonate (1g) with excess sodium thiophenolate in methyl cellosolve, have been studied. They obey the first order rate law and are zero order with respect to the base-nucleophile. However, the ratio of 1,2- and 1,3-elimination to exo-substitution products depends strongly on the base-nucleophile concentration. Ion pair intermediates are indicated. The extreme inertness of 2-norbornyl derivatives in displacement reactions is due to severe steric hindrance of rearside nucleophilic attack, a feature they have in common with other bi- and tricyclic molecules bearing nucleofugal groups adjacent to one or two bridgehead atoms.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640115