Complete reversal in Wacker oxidation of acetonides and cyclic carbonates of allylic diols

Conference · Sun Dec 31 00:00:00 EST 1995

OSTI ID:250088

Kang, Suk-Ku; Jung, Kyung-Yun; Namkoong, Eun-Young ^[1]

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1. Sung Kyun Kwan Univ., Suwon (Korea, Republic of); and others

The palladium(II)-catalyzed oxidation of terminal olefins to give methyl ketones (Wacker prossess) is well established in organic synthetic reactions. However palladium(II)-catalyzed oxidation of acetonide or cyclic carbonate of terminal allylic diol afforded aldehyde or {alpha},{beta}-unsaturated aldehyde as the sole products, resulting of anti-Markovnikov hydration. Alternatively, for the internal olefins of the substituted allylic diols, (E)-allylic diol provided {beta}-keto-product, whereas (Z)-allylic diol afforded {alpha}-keto-product. The acetonides and cyclic carbonates of the substituted allylic diols yielded {beta}-keto-products and {alpha},{beta}-unsaturated ketones.

• OSTI ID: 250088
• Report Number(s): CONF-9508100-; TRN: 96:002623-0026
• Resource Relation: Conference: 8. IUPAC symposium on organometallic chemistry directed towards organic synthesis, Santa Barbara, CA (United States), 6-10 Aug 1995; Other Information: PBD: 1995; Related Information: Is Part Of Eight IUPAC symposium on organometallic chemistry directed towards organic synthesis (OMCOS 8); PB: 375 p.
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
10 SYNTHETIC FUELS
ORGANOMETALLIC COMPOUNDS
CATALYTIC EFFECTS
KETONES
CHEMICAL PREPARATION
PALLADIUM COMPLEXES
OXIDATION