131529-91-4Relevant academic research and scientific papers
Phosphazene base-catalyzed hydroamination of aminoalkenes for the construction of isoindoline scaffolds: Application to the total synthesis of aristocularine
Matsuoka, Junpei,Terashita, Maki,Miyawaki, Akari,Tomioka, Kiyoshi,Yamamoto, Yasutomo
supporting information, (2021/12/30)
A method for isoindoline synthesis via phosphazene base-catalyzed intramolecular hydroamination of aminoalkenes was developed. The reaction has a broad functional group tolerance, including for halide, cyano, and methoxy groups, and could also be used to
Photophysical and photochemical behavior of intramolecular-styrene-amine exciplexes
Lewis, Frederick D.,Dasharatha Reddy,Schneider, Siegfried,Ga, Michael
, p. 3498 - 3506 (2007/10/02)
The photophysical and photochemical behavior of a series of secondary and tertiary ω-(β-styryl)aminoalkanes with one to five methylenes separating the styryl and amino groups has been investigated and compared to the intermolecular reactions of 1-phenylpropene with secondary and tertiary amines. The tertiary styrylamines form fluorescent intramolecular exciplexes, but fail to undergo intramolecular addition reactions. Both the rate constant for exciplex formation and the stability of the exciplex are dependent upon the length of the polymethylene chain connecting the chromophores. The failure of the tertiary amine exciplexes to undergo intramolecular addition is attributed to an unfavorable exciplex geometry for α-C-H transfer to the styrene double bond. While the secondary styrylamines do not form fluorescent exciplexes, the dependence of the styrene singlet lifetime upon the polymethylene chain length is similar to that for the tertiary styrylamines. Intramolecular N-H addition to the styrene double bond results in the formation of two regioisomeric (α-phenyl and α-benzyl) cyclic amines of different ring size. The regioisomer of larger ring size is favored except in the case in which four methylenes separate the chromophores. The effects of polymethylene chain length, solvent polarity, temperature, and the bulk of the N-alkyl group upon product yields and ratios are discussed in terms of a mechanism involving singlet exciplex and biradical intermediates.
INTRAMOLECULAR PHOTOCHEMICAL REACTIONS OF N-ALKYL-5-PHENYL-4-PENTEN-1-AMINES
Lewis, Frederick D.,Reddy, G. Dasharatha
, p. 5293 - 5296 (2007/10/02)
Irradiation of N-alkyl-5-phenyl-4-penten-1-amines results in the formation of intramolecular styrene-amine adducts and disproportionation products.Increasing the bulk of the N-alkyl group increases the regioselectivity of N-H transfer favoring the formation of piperidine vs. pyrrolidine products and favors disproportionation vs. cyclization.
