The stereospecificity of the reduction of 1-methyl-(1a, 2a), 1-methoxy-(1b, 2b), and 1-unsubstituted-7-chloro-7-fluorobicyclo[4.1.0]heptane (1c, 2c) with tri-n-butyltin hydride has been found to decrease in the order (a) > (c) > (b), suggesting that the configurational stability of the α-fluorocyclopropyl radical is affected by the nature of the β-substituents.
T. Ishihara, E. Ohtani and T. Ando, J. Chem. Soc., Chem. Commun., 1975, 367 DOI: 10.1039/C39750000367
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