Summary
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1.
Sterically hindered hydroxy groups in bicyclic systems of the type of cis-peraydroindan and cis-perhydropentalene are not replaced by iodine under the action of (C2H5O)3P· CH3I.
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2.
The conditions for the replacement of secondary hydroxy groups in an open chain by iodine are comparable with the conditions for the replacement of primary hydroxy groups under the action of (C6H5O)3P·CH3I.
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Kochetkov, N.K., Usov, A.I. Monosaccharides. Russ Chem Bull 11, 977–983 (1962). https://doi.org/10.1007/BF00905217
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DOI: https://doi.org/10.1007/BF00905217