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2004
Oxidation
O 0212
44- 052
Synthesis of Carbo- and Heterocyclic Aldehydes Bearing an Adjacent Donor
Group — Ozonolysis versus OsO4/KIO4-Oxidation. — Initial Grignard addition of
olefins (II) and (VIII) to cyclic ketones (I) and (VII) and subsequent methylation of the
resulting tertiary alcohols (III) and (IX) furnish the terminal olefins (V) and (X) as precursors for the aldehyde functionality. Alkenes (V) in which the olefinic moiety is directly attached to a quaternary carbon center are not able to undergo oxidation by
ozonolysis, whereas homologues (X), bearing an additional methylene linker, undergo
smooth oxidation to aldehydes (XI). However, aldehydes (VI) are obtained in moderate
to excellent yields by using KIO4/OsO4. — (MIHOVILOVIC*, M. D.; SPINA, M.;
MUELLER, B.; STANETTY, P.; Monatsh. Chem. 135 (2004) 7, 899-909; Inst. Appl.
Synth. Chem., Tech. Univ., A-1060 Wien, Austria; Eng.) — H. Hoennerscheid
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