Journal of the American Chemical Society

Ground-and excited-state carboxylate radical chain carriers. Radical chain substitution reactions with acyl hypohalites

PS Skell, DD May

Index: Skell, Philip S.; May, Donald D. Journal of the American Chemical Society, 1983 , vol. 105, # 12 p. 3999 - 4008

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Citation Number: 19

Abstract

Abstract: Earlier work with aliphatic carboxylate radicals held no prospect that they could be used as hydrogen abstractors in substitution reactions. Contrary to this expectation, acetoxy, propionoxy, isobutyroxy, and pivaloxy are effective in this role. At low temperatures radical chain brominations of alkanes and haloalkanes occur in satisfactory yields when the acyl hypobromites, RC02Br, are used; the selectivities are independent of the structure of R. ...