5325-95-1Relevant academic research and scientific papers
Redox-Neutral α-Arylation of Alkyl Nitriles with Aryl Sulfoxides: A Rapid Electrophilic Rearrangement
Shang, Li,Chang, Yonghui,Luo, Fan,He, Jia-Ni,Huang, Xin,Zhang, Lei,Kong, Lichun,Li, Kaixiao,Peng, Bo
supporting information, p. 4211 - 4217 (2017/03/27)
A facile α-arylation of nitriles has been developed by simply introducing Tf2O and DABCO to the mixture of nitriles and aryl sulfoxides. The transformation consists of two sequential steps: (i) Tf2O-initiated electrophilic assembly a
METHOD OF CONVERTING ALCOHOL TO HALIDE
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Page/Page column 53; 132; 142; 143, (2017/01/02)
The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.
Titanium-mediated addition of grignard reagents to acyl cyanohydrins: Aminocyclopropane versus 1,4-diketone formation
Setzer, Paul,Forcher, Gwenael,Boeda, Fabien,Pearson-Long, Morwenna S. M.,Bertus, Philippe
supporting information, p. 171 - 180 (2014/01/06)
The 1,2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples), giving both aminocyclopropane derivatives and 1,4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1,4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), the cyclopropane derivatives were obtained in good yields. The observed dichotomy may be explained by a ring-opening of the five-membered titanacycle intermediate followed by a nonselective acyl addition. The 1,2-dianion reactivity of the reagent generated from EtMgBr and Ti(OiPr)4 was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples). When the reaction was performed in diethyl ether, 1,4-diketones were mainly isolated. Under certain conditions, cyclopropane derivatives were also obtained in good yields. A mechanism rationalizing this dichotomy is presented. Copyright
2',3'-O-phosphonoalkylidene derivatives of ribonucleosides: Synthesis and reactivity
Endova, Magdalena,Masojidkova, Milena,Budesinsky, Milos,Rosenberg, Ivan
, p. 11151 - 11186 (2007/10/03)
A novel type of nucleotide analogues, the 2',3'-O-(1- diethylphosphono)alkylidene derivatives of ribonucleosides was prepared by redox reaction of diethyl chlorophosphite with various nucleoside orthoesters. Some of these compounds undergo interesting rearrangements when treated with nucleophiles. The configuration of the title compounds was determined by 2D-ROESY experiments. Biological activity of partially protected nucleotide analogues is also discussed.
3',5'-O-phosphonoalkylidene derivatives of 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine: Synthesis and reactivity
Endova, Magdalena,Masojidkova, Milena,Budesinsky, Milos,Rosenberg, Ivan
, p. 11187 - 11208 (2007/10/03)
Various 3',5'-O-(1-phosphonoalkylidene) derivatives of 1-(2-deoxy-β-D- threo-pentofuranosyl)thymine bearing a substituent in the ω-position of the alkylidene chain were prepared by the redox reaction of diethyl chlorophosphite with six-membered 3',5'-orthoesters of xylo-dT. Susceptibility of ω-haloalkylidene derivatives for nucleophilic substitution is discussed. The configuration of the final phosphonates was determined by 2D-ROESY NMR experiments.
