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Styrene oxide (3c) underwent rearrangement to phenylacetaldehyde during the HRGC analysis (usually 2-10 %, sometimes more). Curiously we did not observe this behavior with α-methylstyrene oxide (3d), although other workers have already reported this: Garin, D.L.; Gamber, M. and Rowe, B.J. J. Chem. Ed. 1996, 73, 555.
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We noted that the yield is somewhat reduced if the iodohydrin was left for a long time under reduced pressure. trans-2-Iodocyclohexanol (2a) was reported to sublime under vacuum: Heilbron, M.I. and Bunbury, H.M. ed. "Dictionary of Organic Compounds", vol II, Oxford University Press, New York, 1943, p. 372.
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Our experience showed that all iodohydrins are sufficiently stable to be handled at room temperature for hours, except for 2b which decomposed to iodine and a mixture of unidentified products after being left at room temperature overnight. All iodohydrins could be stored without decomposition in a freezer for at least one month. In this large scale preparation crystallization may occur for some iodohydrins after some time in the freezer, or just after their preparation.
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R 5.4 min (RTX-5)].
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