Mechanistic and exploratory organic photochemistry. XXXIV. Control of photochemical reaction pathways by excited-state multiplicity

1968 ◽  
Vol 90 (15) ◽  
pp. 4191-4193 ◽  
Author(s):  
H. E. Zimmerman ◽  
R. S. Givens ◽  
R. M. Pagni
1995 ◽  
Vol 73 (6) ◽  
pp. 826-834 ◽  
Author(s):  
Simona G. Merica ◽  
Nigel J. Bunce

A series of nitropolychlorodibenzo-p-dioxins (NPCDDs) was synthesized by condensation between catechols and 2,6-dinitrohalobenzene derivatives. In the presence of sodium ethoxide in anhydrous ethanol, these underwent photochemical SN2Ar* substitutions meta to the nitro group in high chemical yield and moderate quantum yield. Both ring-opening and chloride replacement reactions were observed. The reactions involved the triplet excited state of the NPCDD, and showed a linear relationship between Φ−1 and [nucleophile]−1. Analogous reactions with KCN in methanol showed similar behaviour, but the products could not be isolated. Keywords: photosubstitution, SN2Ar*, dibenzo-p-dioxins.


2009 ◽  
Vol 113 (40) ◽  
pp. 10767-10771 ◽  
Author(s):  
Patrick Z. El-Khoury ◽  
Alexander N. Tarnovsky ◽  
Igor Schapiro ◽  
Mikhail N. Ryazantsev ◽  
Massimo Olivucci

1967 ◽  
Vol 89 (25) ◽  
pp. 6589-6595 ◽  
Author(s):  
Howard E. Zimmerman ◽  
Roger W. Binkley ◽  
John J. McCullough ◽  
Gary A. Zimmerman

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