Zwitterionic biphenyl quinone methides in photodehydration reactions of 3-hydroxybiphenyl derivatives: laser flash photolysis and antiproliferation study

2012 ◽  
Vol 11 (2) ◽  
pp. 381 ◽  
Author(s):  
Nikola Basarić ◽  
Nikola Cindro ◽  
Damir Bobinac ◽  
Lidija Uzelac ◽  
Kata Mlinarić-Majerski ◽  
...  
1996 ◽  
Vol 74 (4) ◽  
pp. 465-475 ◽  
Author(s):  
Peter Wan ◽  
Beverly Barker ◽  
Li Diao ◽  
Maike Fischer ◽  
Yijian Shi ◽  
...  

ortho and para-Quinone methides (2-methylene-3,5-cyclohexadien-1-one and 4-methylene-2,5-cyclohexadien-1-one, respectively) are intermediates in a variety of important chemical systems. In particular, o-quinone methides are useful in synthesis for the construction of chroman ring systems. A brief account of the relevance of quinone methide chemistry will be provided. This is followed by a review of recent studies from our laboratory on efficient methods for the photogeneration of quinone methides, concentrating on the use of hydroxy-substituted benzyl alcohols in aqueous media. It is shown that this method is general since it provides access to o-, m-, and p-quinone methide isomers. When appropriately substituted, all of these quinone methide isomers have been spectroscopically characterized by laser flash photolysis, making this technique the one of choice for studying the dynamics of these reactive intermediates. The mechanism of photochemical generation from hydroxybenzyl alcohols and extensions of the reaction to photogeneration of fluorenyl and biphenyl quinone methides will also be presented. Key words: quinone methide, biphenyl quinone methide, carbocation, photosolvolysis, photodehydroxylation, hetero-Diels–Alder reaction.


2002 ◽  
Vol 76 (5) ◽  
pp. 480 ◽  
Author(s):  
Xavier Damoiseau ◽  
Francis Tfibel ◽  
Maryse Hoebeke ◽  
Marie-Pierre Fontaine-Aupart

2000 ◽  
Vol 72 (4) ◽  
pp. 451 ◽  
Author(s):  
M. Bazin ◽  
F. Bosca ◽  
M. L. Marin ◽  
M. A. Miranda ◽  
L. K. Patterson ◽  
...  

1999 ◽  
Vol 70 (3) ◽  
pp. 292
Author(s):  
Ann Cantrell ◽  
David J. McGarvey ◽  
Louise Mulroy ◽  
T. George Truscott

Author(s):  
M.A. Buntine ◽  
G.J. Gutsche ◽  
W.S. Staker ◽  
M.W. Heaven ◽  
K.D. King ◽  
...  

The technique of laser flash photolysis/laser absorption has been used to obtain absolute removal rate constants for singlet methylene,


1988 ◽  
Vol 66 (2) ◽  
pp. 319-324 ◽  
Author(s):  
R. J. DeVoe ◽  
M. R. V. Sahyun ◽  
Einhard Schmidt ◽  
N. Serpone ◽  
D. K. Sharma

We have studied the anthracene-sensitized photolyses of both diphenyliodonium and triphenylsulphonium salts in solution using both steady-state and laser flash photolysis techniques. Photoproducts, namely, phenylated anthracenes along with iodobenzene or diphenylsulphide, respectively, are obtained from both salts with quantum efficiencies of ca. 0.1 at 375 nm. We infer the intermediacy of diphenyliodo and triphenylsulphur radicals formed by single electron transfer from the singlet-excited anthracene. We have developed a quantitative model of this chemistry, and identify the principal sources of inefficiency as back electron transfer, which occurs at nearly the theoretically limiting rate, intersystem crossing from the initially formed sensitizer–'onium salt encounter complex, and in-cage radical recombination.


1987 ◽  
Vol 52 (25) ◽  
pp. 5512-5517 ◽  
Author(s):  
S. Pratapan ◽  
K. Ashok ◽  
D. R. Cyr ◽  
P. K. Das ◽  
M. V. George

Biochemistry ◽  
1983 ◽  
Vol 22 (23) ◽  
pp. 5270-5279 ◽  
Author(s):  
Anjan Bhattacharyya ◽  
Gordon Tollin ◽  
Michael Davis ◽  
Dale E. Edmondson

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