64198-22-7Relevant articles and documents
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Whitmore et al.
, p. 2028 (1941)
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The Influence of Acetoxy Substituents on the Nucleophilicity of Alkyl Radicals
Giese, Bernd,Engelbrecht, Renate,Erfort, Ulrich
, p. 1289 - 1293 (2007/10/02)
Reduction 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.