Bridgehead free radical stability. The decomposition of t-butylperoxyesters of the 1-adamantyl, 1-bicyclo[2•2•2]octyl, and 1-norbornyl systems
1968 ◽
Vol 46
(19)
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pp. 3099-3103
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The t-butylperoxyesters of 1-adamantyl, 1-bicyclo[2•2•2]octyl, and 1-norbornyl carboxylic acids thermally undergo first order, free radical decomposition in cumene with relative rate constants at 80° of 1.0, 0.07, and 0.001 respectively. As measures of the stability of the derived bridgehead free radicals, the rates span a range much narrower than that for carbonium ion formation at these strained positions. The results are consistent with suggestions that free radicals have smaller force constants for out-of-plane bending than do the corresponding carbonium ions.
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2004 ◽
Vol 467-470
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pp. 1111-1116
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1979 ◽
Vol 20
(2)
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pp. 185-188
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2012 ◽
Vol 204-208
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pp. 3061-3067
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2012 ◽
Vol 1
(10)
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pp. 79
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