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19
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(c) Examples of hydrogenation of tetrasubstituted double bonds conjugated with benzene rings are known (Beilstein database); see, especially: Gray, A. C. G.; Hart, H. J. Am. Chem. Soc. 1968, 90, 2569-2578.
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1842655761
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Based on observation of NOE effects (see Supporting Information).
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21
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85085784132
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1H NMR signals at ca. δ 5 for the benzylic CH-O.
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22
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1842806897
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It is believed that hydrogenolysis is facilitated by development of a partial positive charge on the benzylic carbon;18 siloxy groups have a lowered ability to stabilize an adjacent positive charge.20
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25
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0042689402
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1842806898
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Made from 2,5-dimethylphenol by the method of ref 30, except that the formyl group was best generated by benzylic bromination,31 followed by oxidation with DMSO.32
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39
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