Abstract
Whitmore and Rothrock1 showed that the hydroxyl group in neo-pentyl alcohol has remarkable resistance against replacement by a halogen atom through the agency of thionyl chloride and phosphorus tribromide. Dostrovsky, Hughes and Ingold2 attribute this to steric hindrance to end-on approach to the α-carbon atom. Whitmore and Rothrock, however, leave the impression that neo-pentyl alcohol does not interact at all with these reagents, and indeed state : “The inactivity of neopentyl alcoholto heat and reagents has been demonstrated” ; but the work of Gerrard3 enabled us to predict probability of easy broadside approach.
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References
Whitmore and Rothrock, J. Amer. Chem. Soc., 54, 3431 (1932).
Dostrovsky, Hughes and Ingold, J. Chem. Soc., 173 (1946).
Gerrard, J. Chem. Soc., 688 (1936); 99 (1939); 218 (1940); 85 (1944).
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GERRARD, W., NECHVATAL, A. Neo-pentyl Alcohol and Steric Hindrance. Nature 159, 812–813 (1947). https://doi.org/10.1038/159812b0
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DOI: https://doi.org/10.1038/159812b0
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