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Pregled bibliografske jedinice broj: 303902

Časopis

Autori: Basarić, Nikola; Mitchell, Devin; Wan, Peter
Naslov: Substituent effects in the intramolecular photoredox reactions of benzophenones in aqueos solutions
Izvornik: Canadian Journal of Chemistry (0008-4042) 85 (2007), 9; 561-571
Vrsta rada: članak
Ključne riječi: intramolecular photoredox; acid catalysis; meta effect; benzophenone photochemistry
Sažetak:
A number of α-hydroxy-3-benzylbenzophenones 7-11 have been synthesized for the purpose of studying the effect of a phenyl substituent on the intramolecular photoredox reaction of 3-(hydroxymethyl)benzophenone (5) discovered in our laboratory. This latter compound was found to undergo a unimolecular (formal) intramolecular redox reaction upon photolysis in aqueous acid that results in clean reduction of the benzophenone ketone (to secondary alcohol) and oxidation of the alcohol to aldehyde. Three of the phenyl-substituted compounds with simple phenyl (7), p-methylphenyl (8) and p-methoxyphenyl (9) were found to undergo the acid-catalyzed intramolecular photoredox reaction with the observation that 9 also undergoes a residual photoredox reaction that is not acid-mediated and may involve initial photoinduced electron transfer which is supported by LFP data. The m-methoxyphenyl (10) compound did not undergo the reaction. The trend in observed relative reactivity may be partially rationalized by examining changes in molecular orbital coefficients observed in the calculated HOMO’s and LUMO’s. The photoredox reaction has also been applied twice in succession in a single compound 11 demonstrating that may be useful for sequential photoredox reactions in a multi-functional compound.
Projekt / tema: 098-0982933-2911
Izvorni jezik: ENG
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bazama podataka:
Current Contents Connect (CCC)
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://www.nrcresearchpress.com/doi/abs/10.1139/v07-081
Broj citata:
Altmetric:
DOI: 10.1139/v08-040
URL cjelovitog teksta:
Google Scholar: Substituent effects in the intramolecular photoredox reactions of benzophenones in aqueos solutions
Upisao u CROSBI: Enidija Lukša (eluksa@irb.hr), 23. Kol. 2007. u 12:11 sati



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