Reactions of diethylaluminum cyanide with acyl phosphonates

Download

index.pdf

Date

2010

Author

Sevim, İlhan

Metadata

Show full item record

Item Usage Stats

93
views

50
downloads

This thesis includes reaction of diethylaluminum cyanide with acyl phosphonates. Cyanohidrin O-phosphates are synthesized from easily available acyl phosphonates and diethylaluminum cyanide. Synthesis of cross-benzoin product of acyl phosphonate, α-hydroxy phosphonate and tertiary carbinol are synthesized from the reaction of diethylaluminum cyanide with acyl phosphonates, representatively. Asymmetric syntheses of cyanohydrin and benzoin type reaction of acyl phoshonate are also investigated representatively.

Subject Keywords

Chemistry., Acyl Phosphonate.

URI

http://etd.lib.metu.edu.tr/upload/3/12611557/index.pdf
https://hdl.handle.net/11511/19272

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Synthesis of ferrocenyl quinolines Zora, Metin (Elsevier BV, 2008-06-01) A convenient one-pot synthesis of ferrocenyl-substituted quinolines via a molecular iodine-catalyzed reaction of ferrocenylimines with enolizable aldehydes is reported. First, nucleophilic addition of the in situ generated enol to ferrocenylimine produces beta-anilinopropionaldehyde, which then undergoes intramolecular Friedel-Crafts reaction to give dihydroquinoline derivative. Finally, subsequent dehydration and aerobic oxidation affords ferrocenyl quinolines.
Synthesis of ferrocenyl pyrazoles by the reaction of 3-ferrocenylpropynal with hydrazinium salts Zora, Metin; Odabasoglu, Mustafa; Bueyuekguengoer, Orhan; Turgut, Guenseli (Elsevier BV, 2008-01-01) Synthesis of ferrocenyl-substituted pyrazoles via the reaction between 3-ferrocenylpropynal and hydrazinium salts is described. Depending upon the substitution pattern of hydrazine derivative, the reaction affords 1-alkyl/aryl-5-ferrocenylpyrazoles and/or 1-alkyl/aryl-3-ferrocenylpyrazoles. Structures of 5-ferrocenyl-1-phenyl-1H-pyrazole, 1-benzyl-5-ferrocenyl-1H-pyrazole and 2-(3-ferrocenylpyrazol-1-yl)ethanol were identified by X-ray crystallography.
Synthesis of spiro-containing 1,4-oxazepines from N-propargylic beta-enaminones Karadeniz, Eda; Kelgökmen, Yılmaz; Zora, Metin (2018-03-18) An efficient and general method for the synthesis of spiro‐1,4‐oxazepines and 3,3‐dimethyl‐1,4‐oxazepines is reported. When treated with ZnI2 and AgSbF6 in refluxing DCE, cyclohexane‐embedded N‐propargylic β‐enaminones underwent 7‐exo‐dig cyclization to afford spiro‐1,4‐oxazepines, specifically 12‐methylene‐11‐oxa‐7‐azaspiro[5.6]dodeca‐7,9‐dienes, in good to high yields. Accordingly, N‐(1,1‐dimethyl)propargylic β‐enaminones produced 3,3‐dimethyl‐1,4‐oxazepines. Cyclization was found to be general for a dive...
Synthesis of beta-chloro-alpha-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates Polat-Cakir, Sidika; BEKSULTANOVA, Nurzhan; Doğan, Özdemir (Informa UK Limited, 2018-12-02) A series of unactivated racemic and chiral aziridine-2-phosphonates were synthesized by modified Gabriel-Cromwell reaction. Ring opening reaction of the synthesized phosphonates by gaseous HCl provided access to a wide range of biologically interesting novel beta-chloro-alpha-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields.
Synthesis and reactions of alpha-keto-beta-hydroxyphosphonates Barış, Şehriban; Demir, Ayhan Sıtkı; Department of Chemistry (2007) This thesis presents synthesis and different reactions of alpha-keto-beta-hydroxyphosphonates. Toward this aim, the hydroxyl functionality of alpha-hydroxycarboxylic acids were protected with alkyl or acyl groups and then formation of acid chloride followed by the reaction with trialkylphosphite furnished protected alpha-keto-beta-hydroxyphosponates. Nucleophilic addition reactions were applied to these compounds to obtain quaternary alcohols with phosphonate functionality. The addition reactions were tried...

Citation Formats

İ. Sevim, “Reactions of diethylaluminum cyanide with acyl phosphonates,” M.S. - Master of Science, Middle East Technical University, 2010.