463932-04-9Relevant academic research and scientific papers
Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles
Peterson, Luke J.,Wolfe, John P.
supporting information, p. 2339 - 2344 (2015/07/27)
Modified reaction conditions that facilitate Pd-catalyzed alkene carboamination reactions of electron-deficient nitrogen nucleophiles are reported. Pent-4-enylamine derivatives bearing N-tosyl or N-trifluoroacetyl groups are coupled with aryl triflates to
Electron transfer versus proton transfer in excited states of bichromophoric aniline/olefin systems
Benali, Otman,Miranda, Miguel A.,Tormos, Rosa
, p. 2317 - 2322 (2007/10/03)
Photolysis of 2-allylaniline (1a) and trans-2-cinnamylaniline (2a) produced mainly the five- or the six-membered ring products 3a or 9a, respectively. Compound 1b, the N-acetyl derivative of la, preferentially underwent photo-Fries rearrangement of the anilide moiety, while - in contrast - the analogous compound 2b, derived from 2a, displayed competition between photocyclisation and double-bond isomerisation. The latter process, characteristic of the styrene chromophore, largely predominated in the case of 2c, the N-trifluoroacetyl derivative of 2a, while the allyl analogue 1c was essentially unreactive. The photochemical behaviour of the cis-cinnamyl compounds 7a and 7b was analogous to that of their trans isomers 2a and 2b, although double bond isomerisation occurred to a smaller extent. Thus, the introduction of electron-withdrawing acyl groups decreased photocyclisation. The nature of the excited states involved in the photochemistry of 1a-c, 2a-c and 7a and 7b was studied by fluorescence measurements. The most remarkable observation was the formation of intramolecular charge-transfer exciplexes in the cases of 1a, 2a, 2b, 7a and 7b. The exciplex bands of the cinnamyl compounds 2a, 2b, 7a and 7b in acetonitrile were considerably red-shifted (maxima at ca. 500 nm). A satisfactory correlation of the photochemical and photophysical data could be achieved by considering that photocyclisation took place when clear exciplex emission was observed. Alltogether, the above data strongly supported the involvement of an excited state electron-transfer mechanism in the photocyclisation of aniline/olefin bichromophoric systems. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
The reactivity of polyfunctionalized iminophosphoranes
Carite,Alazard,Ogino,Thal
, p. 7011 - 7014 (2007/10/02)
The reactivity of some functionalized azides has been studied under the conditions of the Staudinger and aza-Wittig reactions. With the azides having a trifluoroacetamido group in the ortho-position of the aromatic ring, intramolecular reactions have been observed which allow new synthetic approaches to indoline and imidazoindole compounds.
