Uncatalyzed addition of TMSCN to acylphosphonates

Demir, Ayhan Sıtkı
Reis, Omer
Kayalar, Metin
Eymur, Serkan
Reis, Barbaros
The cyanosilylations of various alkyl- and arylphosphonates under comparatively mild conditions furnished the trimethyl-silyloxycyanophosphonates in high yield. The addition to ketophosphonate functions works without the influence of a catalyst.


Unusual fragmentation of fulvene endoperoxides with phenyliodosyl bis(trifluoroacetate) (PIFA)
Ozer, G; Saracoglu, N; Balcı, Metin (Wiley, 2003-05-01)
Reaction of unsaturated fulvene endoperoxides with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate gave saturated fulvene endoperoxides containing the 1,2-dihydropyridazine ring. Treatment of dihydropyridazine endoperoxides with water followed by phenyliodosyl bis(trifluoroacetate) oxidation provided acrylic acid derivatives and dimethyl pyridazine-3,6-dicarboxylate.
Simple, mild, and efficient method for the reduction of 1,4-benzoquinones to hydroquinones by the action of NaN3
Algi, Fatih; Balcı, Metin (Informa UK Limited, 2006-08-01)
A simple, mild, and efficient method is presented for the reduction of 1,4-benzoquinones to hydroquinones by the action of NaN3 under neutral conditions in the presence of water.
Catalytic asymmetric nitroaldol (Henry) reaction with a zinc-Fam catalyst
Bulut, Adnan; Aslan, Ayhan; Doğan, Özdemir (American Chemical Society (ACS), 2008-09-19)
Ferrocenyl-substituted aziridinylmethanol (Fam-1) was used as a catalyst with zinc for the asymmetric nitroaldol (Henry) reaction. This catalyst worked with a variety of aldehydes (aromatic, aliphatic, alpha,beta-unsaturated, and heteroaromatic) and alpha-ketoesters to give the nitroaldol product in up to 97% yield and 91% ee. The chiral ligand call be recovered and recycled Without losing its activity.
Asymmetric synthesis of norbornene based 1,4-amino alcohol derivatives and applications in asymmetric transformations
Sünbül, Murat; Tanyeli, Cihangir; Department of Chemistry (2005)
The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene backbone was performed starting with simple and cheap anhydride 30. Quinine-mediated desymmetrization of anhydride 30 with methanol resulted in (2S,3R)-(-)-cis-hemiester 31 (98% e.e.). Chemoselective amination with HMPTA and NH4OH followed by LAH reduction afforded (2S,3R)-(+)-36 and (2S,3R)-(-)-37, respectively. The amidoester (2S,3R)-(-)-32 was transformed into chiral ligand (2S,3R)-(-)-35 with Grignard reaction followed by LAH reduction. T...
Bromination of 5-methoxyindane: Synthesis of new benzoindenone derivatives and ready access to 7H-Benzo[c]fluoren-7-one skeleton
TUTAR, Ahmet; BERKİL AKAR, KIYMET; Hark, Richard R.; Balcı, Metin (Informa UK Limited, 2008-01-01)
The photobromination of 5-methoxyindane and 5-methoxyindanone was studied at both high and low temperatures. 1,2,3-Tribromo-6-methoxyindene was easily synthesized by photolytic bromination of 5-methoxyindane at low temperature. 1,1,2,3-Tetrabromo-6-methoxyindene was obtained from the photobromination of 5-methoxyindan at 77 degrees C, which could then be easily converted to the 2,3-dibromo-6-methoxyindene by silver-supported hydrolysis. Photochemical bromination of 5-methoxy-1-indanone with N-bromosuccinimi...
Citation Formats
A. S. Demir, O. Reis, M. Kayalar, S. Eymur, and B. Reis, “Uncatalyzed addition of TMSCN to acylphosphonates,” SYNLETT, pp. 3329–3333, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56907.