ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The Influence of Acetoxy Substituents on the Nucleophilicity of Alkyl RadicalsReduction of the organomercuric salt 3 with NaBH4 yields the acetoxy-substituted radical 4. Using competition techniques the rel. rates of addition of 4 to alkenes 5 can be measured. The rate data show that radical 4 is a nucleophile (table 1) but the nucleophilicity is slightly smaller than that of the sec. cyclohexyl radical (figure 1). The acetoxy group, therefore, acts as an electron withdrawing substituent that reduces the nucleophilic reactivity and the nucleophilic selectivity of alkyl radicals.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19851180345
Permalink