OXIDATION OF ARYL ALKYL KETONES TO ALPHA-ACYLOXY, ALPHA-(CAMPHORSULFONYLOXY), OR ALPHA-HYDROXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS OR (1S)-(+)-10-CAMPHORSULFONIC ACID

Date

1990-01-01

Author

DEMIR, AS
CAMKERTEN, N
AKGUN, H
Tanyeli, Cihangir
MAHASNEH, AS
WATT, DS

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The α-oxidation of aryl alkyl ketones using manganese(III) acetate in the presence of various carboxylic acids and (1S)-(+)-10-camphorsulfonic acid provided a convenient synthesis of α-acyloxy, α-(10-camphorsulfonyloxy), and α-hydroxy derivatives in good yield.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/42577

Journal

SYNTHETIC COMMUNICATIONS

DOI

https://doi.org/10.1080/00397919008053170

Collections

Department of Chemistry, Article

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THE ALPHA'-OXIDATION OF ALPHA-ALKOXY ENONES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS Demir, Ayhan Sıtkı; SAATCIOGLU, A (Informa UK Limited, 1993-01-01) The alpha'-oxidation of cyclic derivatives of alpha-alkoxy-alpha,beta-unsaturated ketones using manganese(III)acetate in the presence of various carboxylic acids provided a convenient synthesis of 5-acyloxy-2-alkoxy-2-cyclopentenones and 6-acyloxy-2-alkoxy-2-cyclohexenones.
Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005) A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
A facile synthesis of various butenolides Tanyeli, Cihangir (Informa UK Limited, 2000-01-01) The synthesis of alpha'-acyloxy-alpha,beta-unsaturated cyclic ketones from the corresponding alpha,beta-unsaturated cyclic ketones by using manganese (III) acetate in combination with 2-chloropropionic acid followed by subsequent Arbuzov and intramolecular Horner-Emmons cyclization reactions provided a convenient synthetic pathway to various butenolides 4a-d.
Synthesis of chiral lactones via the baeyer villiger oxidation of cyclic aromatic acetoxy ketones novel annulation reactions of 2-propynyl-1,3-dicarbonyl compounds to form pyrroles addition of acyl phosphonates to diethyl cyanophosphonate (depc) Aybey, Asuman; Demir, Ayhan Sıtkı; Department of Chemistry (2009) Chiral Baeyer-Villiger (BV) oxidation of cyclic ketones allows rapid access to asymmetric lactones as valuable intermediates in organic chemistry and frequently encountered precursors in enantioselective synthesis. In the first part, BV oxidation of functionalized ketones, especially cyclic -hydroxy and acetoxy ketones is described which could be a straightforward route to the -hydroxy lactones and -hydroxyalkanoic acid derivatives. The -acetoxylation of indanone, tetralone and chromanone derivatives by usi...
Reactions of 2-substituted epichlorohydrins Tanyeli, Cihangir; Akhmedov, IM; Ozgul, E; Kandemir, CG (Informa UK Limited, 1996-01-01) 2-Substituted epichlorohydrins have been synthesized by starting with 1,2-dichloro acetone and various alkyl and aryl halides via dichlorohydrins followed by cyclization. The reactive 2-substituted epichlorohydrins were subjected to nucleophilic attacking of azide and cyanide ions to afford corresponding beta-azido alcohols and alpha,beta-unsaturated nitriles.

Citation Formats

A. DEMIR, N. CAMKERTEN, H. AKGUN, C. Tanyeli, A. MAHASNEH, and D. WATT, “OXIDATION OF ARYL ALKYL KETONES TO ALPHA-ACYLOXY, ALPHA-(CAMPHORSULFONYLOXY), OR ALPHA-HYDROXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS OR (1S)-(+)-10-CAMPHORSULFONIC ACID,” SYNTHETIC COMMUNICATIONS, pp. 2279–2289, 1990, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42577.