117714-41-7Relevant articles and documents
Laser photolysis of naphthoquinone diazide in cyclohexane - two-laser chemistry
Bendig,Mitzner
, p. 1004 - 1008 (1994)
The laser photochemistry of 1,2-naphthoquinone-diazide-(2)-5-sulfonic acid phenylester in cyclohexane has been investigated. The photolysis experiments have been done using a KrF laser pulse (generation pulse) and a nitrogen laser pulse (transformation pulse) with various time delay from 40 ns up to 1 s. At a time delay between the two laser pulses in the μs-region, the formation of indene and cyclohexyl-indene derivatives has been observed, additional to the corresponding indenecarboxylic acid. The laserspecific formation of these compounds is the result of the electronic excitation of the intermediately formed ketene and its reaction by decarbonylation. The time delay for getting a high yield of the indene and the cyclohexyl-indene derivatives correlates closely with the rise time and the life time of the ketene.
On the photodecomposition mechanism of o-diazonaphthoquinones
Barra, Mónica,Fisher,Cernigliaro,Sinta,Scaiano
, p. 2630 - 2634 (2007/10/02)
The mechanism for the photodecomposition of several o-diazonaphthoquinones has been examined in acetonitrile solution using time-resolved laser flash photolysis techniques. It is concluded that the Wolff rearrangement, which involves the formation of a ketene intermediate, can be regarded as a concerted process in the nanosecond time scale. It is suggested that the reaction of the ketene with water, which is well known to yield 3-indenecarboxylic acids, involves the intermediacy of a ketene hydrate. Pyridine, a molecule frequently employed as a carbene trap/probe, efficiently traps the ketene in these systems; this scavenging reaction can be employed as a probe for the study of the dynamics of ketene reactions, but in some systems it may represent a problem in carbene studies if the possibility of ketene reactions is not considered.
Synthesis and Characterization of Substituted 2-Diazo-1-oxo-1,2-dihydronaphthalenes and Their Products of Photolysis and Thermolysis
Baumbach, B.,Bendig, J.,Nagel, T.,Dubsky, B.
, p. 625 - 635 (2007/10/02)
Several 2-diazo-1-oxo-1,2-dihydronaphthalenes (1, 2) have been synthesized by reaction of selected hydroxy compounds and 2-diazo-1-oxo-1,2-dihydronaphthalene-5- and -4-sulfonylchloride, respectively.Photolysis as well as thermolysis of 1 and 2 leads to final products, the nature of which depends on the position of substitution.So, reactions of 5-substituted derivatives (1) yield the corresponding indene-3-carboxylic acids 3 and their esters 5, respectively.In contrast, reactions of 4-substituted derivatives (2) lead to the formation of the 1-sulfo-indene-3-carboxylic acid derivatives 4 and 6.Prepared compounds have been characterized by means of mass, ultraviolet, infrared, 1H-n.m.r. and 13C-n.m.r. spectroscopy.
