Difunctional and heterocyclic products from the ozonolysis of conjugated C sub 5 -C sub 8 cyclodienes

Journal Article · Thu Nov 22 23:00:00 EST 1990 · Journal of Organic Chemistry; (United States)

DOI:https://doi.org/10.1021/jo00311a021· OSTI ID:5122882

Griesbaum, K; Jung, In Chan; Mertens, H ^[1]

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1. Univ. Karlsruhe (Germany)

Ozonolyses of the conjugated C{sub 5}-C{sub 8} cyclodienes 1a-d in methanol, followed by reduction with DMS, have been examined. Monoozonolyses gave the corresponding unsaturated dialdehydes 2e as the primary products. In subsequent reactions, the dialdehydes 2e derived from the monoozonolyses of 1a, 1b, and 1c gave in high yields the heterocyclic compounds 7, 8k, and 9k, respectively. Diozonolyses of 1a-d gave the corresponding dialdehydes 3e as the primary products. In subsequent reactions, the dialdehydes 3e derived from 1b and 1c gave the heterocyclic compounds 8l, and 9l, respectively. In addition, aldehydes 2e and 3e underwent partial acetalization reactions with methanol.

• OSTI ID: 5122882
• Journal Information: Journal of Organic Chemistry; (United States), Journal Name: Journal of Organic Chemistry; (United States) Vol. 55:24; ISSN JOCEA; ISSN 0022-3263
• Country of Publication: United States
• Language: English

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ACETALS
ADSORBENTS
ALDEHYDES
ALKENES
AMINES
AROMATICS
BENZENE
CATALYSIS
CATALYSTS
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CYCLOALKENES
CYCLOPENTADIENE
DIENES
DMSO
ETHERS
GAS CHROMATOGRAPHY
HETEROCYCLIC COMPOUNDS
HOMOGENEOUS CATALYSIS
HYDROCARBONS
HYDROGENATION
HYDROXY COMPOUNDS
ISOMERS
KINETICS
LIQUID COLUMN CHROMATOGRAPHY
MASS SPECTRA
MASS SPECTROSCOPY
MOLECULAR STRUCTURE
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OZONE
PHENOL
PHENOLS
POLYENES
REACTION KINETICS
REDUCTION
SEPARATION PROCESSES
SILICA GEL
SPECTRA
SPECTROSCOPY
SULFOXIDES
SYNTHESIS