The hydrogens at C(2) in spiro[2.n]alkanes are abstracted above five times more rapidly than ‘normal’ secondary hydrogens by t-butoxyl radicals, because of favourable overlap of the p-orbital at C(2) with the HOMO of the adjacent cyclopropyl ring; the hydrogenes at C(2) in bicyclo[n.1.0]alkanes are less activated because the cyclopropyl ring orientation is less favourable for overlap.
C. Roberts and J. C. Walton, J. Chem. Soc., Chem. Commun., 1984, 1109 DOI: 10.1039/C39840001109
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