Radical cyclizations of 2-(ω-haloalkylthio)enones to thiapolycycloalkanones

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2279-2282

  Ponaras, Anthony A ^a   Zaim, Ömer ^a  

^a CATHOLIC UNIVERSITY OF AMERICA   (United States)

Author keywords

Cyclization; Enones; Heterocyclic compounds; Polyheterocyclic compounds; Radicals and radical reactions; Sulfur heterocycles; sulfenyl ketones

Indexed keywords

CYCLOALKANONE; HALOOLEFIN; HETEROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON; RADICAL;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CONFORMATION; CYCLIZATION; STEREOCHEMISTRY;

EID: 0034175641     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00161-1     Document Type: Article

References (26)

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3. Preparation of 6s: rxn of 2-bromo-2-cyclohexen-1-one with potassium 2-iodobenzyl thiolate in THF (cf., Fujisawa, T.; Sakai, K.; Shirokata, H.; Fukushima, A. (Sagami Chemical Research Center) Jpn. Kokai Tokkyo Koho JP 54,088,210 (1977) Chem. Abstr. 1979, 92, 76093c. Preparation of 10: heating 1,2-cyclohexanedione and 3-chloro-1-propanethiol in benzene (cat. TsOH) under a Dean-Stark trap, followed by treatment with sodium iodide in acetone. Preparation of 13, 14, 17 and 21: rxn of 2,3-epoxycyclohexanone with the appropriate sodium thiolate in ethanol (cf., Tobias, M. A.; Strong, J. G.; Napier R. P. J. Org. Chem. 1970, 35, 1709. Preparation of 18: rxn of 2,3-epoxycyclohexanone with sodium 2-hydroxymethyl benzenethiolate in ethanol, followed by treatment with chlorotrimethylsilane/HMDS, followed by treatment with iodotrimethylsilane.
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