53244-01-2Relevant academic research and scientific papers
Unusual visible-light photolytic cleavage of tertiary amides during the synthesis of cyclolignans related to podophyllotoxin
Lisiecki, Kamil,Krawczyk, Krzysztof K.,Roszkowski, Piotr,Maurin, Jan K.,Budzianowski, Armand,Czarnocki, Zbigniew
, p. 6316 - 6328 (2017/10/06)
During the attempted photochemical cyclization of 2,3-bisbenzylidene-γ-hydroxybutyric acid cyclic amide ester, it was observed that a γ-butyrolactone ring was formed, which was concurrent with the release of the amine fragment from the amide. The process occurs with high yield giving rise to the formation of β-apopicropodophyllin and its regioisomer. Additional experiments confirmed the photochemical nature of this transformation, and that it is independent from the photocyclization of the benzylidene groups – a typical reactivity for the members of the fulgide family. In contrast to the latter UV-driven cyclization, the photochemical cleavage of the amide was proven to proceed under irradiation with visible light.
Total synthesis of (±) maculalactone A, maculalactone B and maculalactone C and the determination of the absolute configuration of natural (+) maculalactone A by asymmetric synthesis
Brown, Geoffrey D.,Wong, Ho-Fai
, p. 5439 - 5451 (2007/10/03)
Maculalactones A, B and C from the marine cyanobacterium Kyrtuthrix maculans are amongst the only compounds based on the tribenzylbutyrolactone skeleton known in nature and (+) maculalactone A from the natural source possesses significant biological activ
Photochromic systems. Part 1. Structural and spectroscopic study of photochromically active products of Stobbe condensation. 2,3-Dibenzylidenesuccinic acid and its anhydride
Davidse, P. Adriaan,Dillen, Jan L. M.,Heyns, Anton M.,Modro, Tomasz A.,Rooyen, Petrus H. van
, p. 741 - 746 (2007/10/02)
E,E-2,3-Dibenzylidenesuccinic acid (2) and its anhydride (1) were synthesized, their crystal structures and 1H and 13C nuclear magnetic resonance spectra were determined, and electron charge densities of carbon atoms were calculated.These results were rel
Direct and Sensitized Photoisomerization of α, δ- Phenylfulgides
Ilge, H.-D.,Paetzold, R.
, p. 705 - 720 (2007/10/02)
The photoreactions starting from the E- and E-E-isomers of mono-, di-, tri- and tetra-(substituted-)phenylfulgides are investigated.The phenylfulgides show strong steric interactions in the molecular framework.For that reason internal conversion is the main deactivation process which increases in the series of mono-, tri- and tetraphenylfulgides.The α, δ-di-(substituted-)-phenylfulgides show the highest photoreactivity.At room temperature in no case luminescence is observed from any E(E-E)-, Z(E-Z, Z-E)- or Z-Z-phenylfulgid isomer of the substances under study.Intersystem crossing cannot compete neither with thermal deactivation nor can it be observed by applying both the internal and external heavy atom effect.The phenylfulgides show typical ??*-photoreactivity: in the singlet state E-Z-isomerization about one double bond competes with electrocyclic ring closure; in the triplet state only simultaneous E-Z-isomerization about the two double bonds is observed.The steric and electronic substituent influences on the photoreactivity are interpreted.A first qualitative model of the isomerization reactions of the fulgides in the excited states is established.
