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Pregled bibliografske jedinice broj: 904540

Časopis

Autori: Škalamera, Đani; Blažek Bregović, Vesna; Antol, Ivana; Bohne, Cornelia; Basaric, Nikola
Naslov: Hydroxymethylaniline photocages for carboxylic acids and alcohols
Izvornik: Journal of organic chemistry (0022-3263) 82 (2017), 23; 12554-12568
Vrsta rada: članak
Ključne riječi: anilines, carbocation, laser flash photolysis, photocage, photochemistry, protective groups
Sažetak:
ortho-, meta- and para-Hydroxymethylaniline methyl ethers 3-5-OMe and acetyl derivatives 3- 5-OAc were investigated as potential photocages for alcohols and carboxylic acids, respectively. The measurements of photohydrolysis efficiency showed that the decaging from ortho- and meta-derivatives takes place efficiently in aqueous solution, but not for the para-derivatives. Contrary to previous reports, we showthat the meta-derivatives are better photocages for alcohols, whereas ortho- derivatives are better protective groups for carboxylic acids. The observed differences were fully disclosed by mechanistic studies involving fluorescence measurements and laser flash photolysis (LFP). Photoheterolysis for the para-derivatives does not take place, whereas both meta- and ortho-derivatives undergo heterolysis and afford the corresponding carbocations 3-C and 4-C. The ortho-carbocation 4-o-C was detected byLFP in aqueous solution (λmax = 410 nm, τ ≈ 90 μs). Moreover, spectroscopic measurements for the meta-acetyl derivative 3-m-OAC indicated the formation of cation in the excited state. The application of ortho- aniline derivative as protective group was demonstrated by synthesizing several derivatives of carboxylic acids. In all cases, the photochemical deprotection was accomplished in high yields (>80%). This mechanistic study fully rationalized photochemistry of aniline photocages which is important for design of new photocages and has potential for synthetic, biological and medicinal applications.
Projekt / tema: HRZZ-IP-2014-09-6312
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
MEDLINE
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://pubs.acs.org/doi/10.1021/acs.joc.7b02314
Broj citata:
Altmetric:
DOI: 10.1021/acs.joc.7b02314
URL cjelovitog teksta:
Google Scholar: Hydroxymethylaniline photocages for carboxylic acids and alcohols
Upisao u CROSBI: Enidija Lukša (Enidija.Luksa@irb.hr), 10. Stu. 2017. u 08:48 sati
Napomene:
This work is financed by the Croatian Academy of Sciences (HAZU)



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