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Volumn 59, Issue 7, 2003, Pages 947-957

A convenient route to 1,4-monoprotected dialdehydes, 1,4-ketoaldehydes, γ-lactols and γ-lactones through radical alkylation of α,β-unsaturated aldehydes in organic and organic-aqueous media

Author keywords

Aldehydes; Alkylation; Photochemistry; Radical and radical reactions; Reactions in water

Indexed keywords

1,3 DIOXOLANE; 1,3 DIOXOLANE DERIVATIVE; 2 HEXENAL; 2 PROPANOL; ALCOHOL; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; BENZOPHENONE; CROTONALDEHYDE; GAMMA LACTONE DERIVATIVE; HYDROGEN; METHANOL; ORGANIC SOLVENT; PHOTOSENSITIZING AGENT; SULFONIC ACID DERIVATIVE;

EID: 0037429034     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01659-9     Document Type: Article
Times cited : (35)

References (73)
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    • 4e from the photolysis of thiones derivatives. C-C bond formation has been exploited mainly for polymerization.
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    • See for example the literature quoted in Ref. 8b.
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    • Compound 3bk was liable to trans-acetalization and oxidation; see Section 5.
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    • NMR spectra of lactols 5 showed no signals attributable to open-chain γ-hydroxyaldehydes and the equilibrium in Scheme 3 was almost completely shifted to the hemiacetalic form.
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    • When hydrogen abstraction is inefficient, radical-radical coupling between the adduct radical and the ketyl radical from the sensitiser occurred to some extent (small amount of compounds of such structure were detected by NMR as impurities of the alkylated products in some fractions from column chromatography).
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    • Purity was determined by UV spectra with comparison with a benzophenone solution.
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    • note
    • 13C NMR spectra of the demethylated analogues of cis and trans 6eq, see Ref 41b,c. cis:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.