63806-53-1Relevant 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.
Reaction of Ketone Alkylhydrazones with Phosphorus Trichloride: a General Mild Route to Substituted Pyrroles
Baccolini, Graziano
, p. 1053 - 1056 (2007/10/02)
A new convinient and mild procedure for the synthesis of symmetrically and unsymmetrically substituted pyrroles is described.This one-pot synthesis consists of two different stages.The first stage, addition of PCl3 to an alkylhydrazone, is always carried out at room temperature.The second stage, addition of an enolizable ketone to the previous reaction mixture, is performed at room temperature, or at 80 deg C under reduced pressure.The results provide clear evidence that diazaphsphole derivatives being formed in the first stage are intermediates in this pyrrole synthesis.
Synthesis of Pyrroles under Mild Conditions using PCl3, Ketones, and Alkylhydrazines
Baccolini, Graziano,Sandali, Claudio
, p. 788 - 789 (2007/10/02)
A one-pot synthesis of symmetrical pyrroles was obtained by reaction of alkylhydrazones of enolizable ketones, PCl3, and subsequent addition of the same ketone.
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.
