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note
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Commercially available starting material (ethyl 3-phenylglycidate) is a mixture of 14% cis, 85% trans, and an unidentified impurity (1%) as established by GC-MS, SPB-5 column. The mixture can be separated by chromatography, with the cis isomer eluting first. The ring opening and the following oxidation reactions can also be carried with the commercial mixture of the cis and trans ethyl-3-phenylglycidate since the trans and cis oxazolidines are also easily separated by chromatography.
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34249896075
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note
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The oxazolidine ring has an envelope conformation with the O atom out of the plane formed by the four other atoms. The torsion angles inside the five-membered ring are N3-C4-C5-O1 = -26.4(4)°, C4-C5-O1-C2 = 43.5(4)°, C5-O1-C2-N3 = -42.7(4)°, O1-C2-N3-C4 = 25.5(4)°, and C2-N3-C4-C5 = 0.9(4)°. The N-C bond distances inside the ring are 1.456(6) and 1.463(6) Å, while the N-C11 is shorter (1.395(6) Å). In the oxazolidine ring, the C-O bonds are 1.400(6) and 1.434(5) Å, while the C-C bond is 1.553(6) Å. For the ester group, the C{double bond, long}O bond (ave. 1.201(5) Å) is shorter than the C-O bond (ave. 1.340(5) Å) as expected. The H atoms on C4 and C5 are cis to each other. The molecules are stabilized in the crystal only by van der Waals interactions. The CIF tables of the crystal 4b have been deposited in the Cambridge Data File Centre. The deposit number is CCDC 619250. This material is available free of charge via the Internet at http://pubs.acs.org.
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