125877-37-4Relevant academic research and scientific papers
Titanium(III) Chloride Mediated Reduction of 1-Nitro-2-phenylethenes
Sera, Akira,Fukumoto, Shoji,Tamura, Masako,Takabatake, Kiyoshi,Yamada, Hiroaki,Itoh, Kuniaki
, p. 1787 - 1791 (2007/10/02)
The reaction of 1-nitro-2-phenylethenes (β-nitrostyrenes) with aqueous titanium(III) chloride afforded substituted pyrroles in addition to the expected reduction products, oximes and carbonyl compounds. 2-Substituted 1-nitro-2-phenylethenes yielded divinylamine derivatives instead of pyrroles.The reaction mechanism has been rationalized by taking account of the electron transfer from titanium(III) species to the nitro olefines, followed by protonation, dimerization, cyclization, and/or hydrolysis.
Silylamines in Organic Synthesis. Reactivity of N,N-Bis(silyl) Enamines toward Electrophiles. A Route to Substituted 2-Aza-1,3-butadienes and Pyridines
Corriu, Robert J. P.,Moreau, Joel J. E.,Pataud-Sat, Magali
, p. 2878 - 2884 (2007/10/02)
N,N-Bis(silyl) enamines appeared to be weak nucleophilic reagents and exhibited a very low reactivity toward electrophiles.However, in the presence of a nucleophilic catalyst, nucleophilic activation of the silicon-nitrogen bond was observed.Under fluoride ion catalysis (TBAF or CsF), N,N-bis(silyl) enamines reacted with carbonyl compounds to give substituted 2-aza-1,3-butadienes.Good yields were obtained in reactions with aromatic aldehydes or ketones.In the case of aliphatic carbonyl compounds, 2-aza 1,3-dienes were only formed in moderate yields.Interestingly, enamidines were easily obtained in high yields upon reactions of dimethylformamide in the presence of MeONa as catalyst.The reaction of aromatic α,β-unsaturated ketones gave 2-aza 1,3,5-trienes, which were not isolated but underwent an intramolecular cycloaddition reaction with regioselective formation of substituted 2,4-diarylpyridines.
TITANIUM TRICHLORIDE MEDIATED REDUCTION OF NITROSTYRENES
Sera, Akira,Fukumoto, Shoji,Yoneda, Takako,Yamada, Hiroaki
, p. 697 - 702 (2007/10/02)
Reactions of substituted nitrostyrenes with aqueous titanium trichloride afforded pyrroles, carbonyl compounds, and oximes.In some instances, divinylamines were produced as well.The reaction mechanism is rationalized taking account of electron transfer to nitroethylenes from Ti(III), followed by protonation, dimerization, cyclization, and hydrolysis.
