ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Selectivity in the Reaction of Carbocations with Nucleophiles, 2. Solvolytic Mechanisms of 7-Norbornyl TrifluoromethanesulfonatesThe reactions of 7,7-bis(trifluoromethylsulfonyloxy)norbornane (4) with several metal cyanides in dipolar aprotic solvents are studied. The results obtained (Table 1) lead to the conclusion that the solvolysis of 7-substituted 7-norbornyl trifluoromethanesulfonates takes place either according to a kc mechanism or with fission of the S — O bond. In no instance is a C — O fission following an SN2 mechanism to be expected. - The selectivity of the reaction of the intermediate carbocations with nucleophiles cannot be explained by means of N+ correlations nor by the reactivity-selectivity relationship, but can be rationalized according to the HSAB principle.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19851180632
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