Mechanistic Aspects of Photoinduced Rearrangement of 2,3-Diarylcyclopentenone Bearing Benzene and Oxazole Moieties

2018 ◽  
Vol 122 (36) ◽  
pp. 7107-7117 ◽  
Author(s):  
Evgeni M. Glebov ◽  
Natalia V. Ruban ◽  
Ivan P. Pozdnyakov ◽  
Vjacheslav P. Grivin ◽  
Victor F. Plyusnin ◽  
...  
Keyword(s):  
Photoinduced Rearrangement

Photoinduced rearrangement of hydroxymethylisoxazolines, a route to enaminoaldehydes

1986 ◽  
Vol 51 (10) ◽  
pp. 2167-2180 ◽  
Author(s):  
Lubor Fišera ◽  
Nadezhda D. Kozhina ◽  
Peter Oravec ◽  
Hans-Joachim Timpe ◽  
Ladislav Štibrányi ◽  
...  
Keyword(s):  
Thionyl Chloride ◽  
Quantum Yields ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Photoinduced Rearrangement ◽  
Condensed Heterocycles

3-Aryl-4-R-carbamoyl-5-hydroxymethylisoxazolines (IV) were synthesized by allowing R-NH2 amines with R = H, CH3, C3H7, C6H5C2H5, and NH2 to act on 3-(X-phenyl)-4-oxo-3a,4,6,6a-tetrahydrofuro[3,4-d]isoxazoles (III) with X = H, 4-CH3, 4-OCH3, 2-OCH3, 4-Cl, 2-Cl, 4-F, 2-F, 4-Br, 4-NO2, and 3-NO2. Exposed to radiation, the substances IV give Z-2-hydroxymethylamino-2-aryl-1-formylacrylamides (V) in good yields. The 4-Cl and 4-F substituted Z-derivatives V isomerize irreversibly to the E-derivatives VI if allowed to stand in solvent; the remaining derivatives V are stable. The quantum yields of the photoreaction are from 0.012 to 0.106 in dependence on the substituent X. In all cases where the compounds IV were used for the preparation of condensed heterocycles in conditions of acid-catalyzed reactions, lactones III were preferentially formed; the action of thionyl chloride on IV results in the formation of chloromethyl derivatives VIII, which do not undergo further cyclization.

ChemInform Abstract: Photoinduced Rearrangement of Carbocyclic 2-Phenylthio-1,3-diols to Deoxysugars.

ChemInform ◽  
2010 ◽  
Vol 26 (17) ◽  
pp. no-no
Author(s):  
D. GRAVEL ◽  
L. FARMER ◽  
R. C. DENIS ◽  
E. SCHULTZ
Keyword(s):  
Photoinduced Rearrangement

scholarly journals Interconversion of the Pallambins through Photoinduced Rearrangement

2012 ◽  
Vol 14 (24) ◽  
pp. 6382-6382
Author(s):  
Jiao-Zhen Zhang ◽  
Rong-Xiu Zhu ◽  
Gang Li ◽  
Li-Ning Wang ◽  
Bin Sun ◽  
...  
Keyword(s):  
Photoinduced Rearrangement

Correction to “Photoinduced Rearrangement of AromaticN-Chloroamides to Chloroaromatic Amides in the Solid State. Inverted ΠN–ΣNOccupational Stability of Amidyl Radicals”

2011 ◽  
Vol 115 (28) ◽  
pp. 8181-8181 ◽  
Author(s):  
Panče Naumov ◽  
Yildiray Topcu ◽  
Mirjana Eckert-Maksić ◽  
Zoran Glasovac ◽  
Fabijan Pavošević ◽  
...  
Keyword(s):  
Solid State ◽  
Photoinduced Rearrangement
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