Photochemistry of S-Phenacyl Xanthates

J 2011

Photochemistry of S-Phenacyl Xanthates

TAZHE VEETIL, Aneesh; Tomáš ŠOLOMEK; Bokolombe Pitchou NGOY; Nela PAVLÍKOVÁ; Dominik HEGER et al.

Základní údaje

Originální název

Photochemistry of S-Phenacyl Xanthates

Autoři

TAZHE VEETIL, Aneesh; Tomáš ŠOLOMEK; Bokolombe Pitchou NGOY; Nela PAVLÍKOVÁ; Dominik HEGER a Petr KLÁN

Vydání

Journal of Organic Chemistry, Columbus, OH, USA, the American Chemical Society, 2011, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 4.450

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/11:00050098

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.1021/jo201385b

UT WoS

000295816700010

Klíčová slova anglicky

Reversible addition-fragmentation transfer; RAFT; macromolecular design via the interchange of xanthates; MADIX; xanthates; phenacyl compounds; photochemistry; photoremovable protecting groups; laser flash spectroscopy; DFT calculations.

Štítky

AKR, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 1. 4. 2015 22:19, prof. RNDr. Petr Klán, Ph.D.

Anotace

V originále

Various synthetically readily accessible S-phenacyl xanthates are shown to undergo photoinitiated homolytic scission of the C-S bond in the primary step. The resultant fragments, phenacyl and xanthic acid radicals, recombine to form symmetrical 1,4-diketones and xanthogen disulfides, respectively, in high to moderate chemical yields in chemically inert solvents. They can also be efficiently trapped by a hydrogen-atom donating solvent to give acetophenone and xanthic acid derivatives. The latter compound is in situ thermally converted to the corresponding alcohol in high chemical yields. S-Phenacyl xanthates could thus be utilized as synthetic precursors to the above mentioned compounds, or as photoremovable protecting groups for alcohols, in which the xanthate moiety represents a photolabile linker. The photochemically released phenacyl radical fragments efficiently but reversibly add to the thiocarbonyl group of the parent xanthate molecule.

Návaznosti

ED0001/01/01, projekt VaV

Název: CETOCOEN

GA203/09/0748, projekt VaV

Název: Nové fotoaktivovatelné sloučeniny pro organickou chemii a biologii

Investor: Grantová agentura ČR, Nové fotoaktivovatelné sloučeniny pro organickou chemii a biologii

MSM0021622413, záměr

Název: Proteiny v metabolismu a při interakci organismů s prostředím

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Proteiny v metabolismu a při interakci organismů s prostředím

Citovat

TAZHE VEETIL, Aneesh; Tomáš ŠOLOMEK; Bokolombe Pitchou NGOY; Nela PAVLÍKOVÁ; Dominik HEGER a Petr KLÁN. Photochemistry of S-Phenacyl Xanthates. Journal of Organic Chemistry. Columbus, OH, USA: the American Chemical Society, 2011, roč. 76, č. 20, s. 8232-8242. ISSN 0022-3263. Dostupné z: https://doi.org/10.1021/jo201385b.

@article{955976,
   author = {Tazhe Veetil, Aneesh and Šolomek, Tomáš and Ngoy, Bokolombe Pitchou and Pavlíková, Nela and Heger, Dominik and Klán, Petr},
   article_location = {Columbus, OH, USA},
   article_number = {20},
   doi = {https://doi.org/10.1021/jo201385b},
   keywords = {Reversible addition-fragmentation transfer; RAFT; macromolecular design via the interchange of xanthates; MADIX; xanthates; phenacyl compounds; photochemistry; photoremovable protecting groups; laser flash spectroscopy; DFT calculations.},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {Photochemistry of S-Phenacyl Xanthates},
   volume = {76},
   year = {2011}
}

TY  - JOUR
ID  - 955976
AU  - Tazhe Veetil, Aneesh - Šolomek, Tomáš - Ngoy, Bokolombe Pitchou - Pavlíková, Nela - Heger, Dominik - Klán, Petr
PY  - 2011
TI  - Photochemistry of S-Phenacyl Xanthates
JF  - Journal of Organic Chemistry
VL  - 76
IS  - 20
SP  - 8232-8242
EP  - 8232-8242
PB  - the American Chemical Society
SN  - 00223263
KW  - Reversible addition-fragmentation transfer
KW  - RAFT
KW  - macromolecular design via the interchange of xanthates
KW  - MADIX
KW  - xanthates
KW  - phenacyl compounds
KW  - photochemistry
KW  - photoremovable protecting groups
KW  - laser flash spectroscopy
KW  - DFT calculations.
N2  - Various synthetically readily accessible S-phenacyl xanthates are shown to undergo photoinitiated homolytic scission of the C-S bond in the primary step. The resultant fragments, phenacyl and xanthic acid radicals, recombine to form symmetrical 1,4-diketones and xanthogen disulfides, respectively, in high to moderate chemical yields in chemically inert solvents. They can also be efficiently trapped by a hydrogen-atom donating solvent to give acetophenone and xanthic acid derivatives. The latter compound is in situ thermally converted to the corresponding alcohol in high chemical yields. S-Phenacyl xanthates could thus be utilized as synthetic precursors to the above mentioned compounds, or as photoremovable protecting groups for alcohols, in which the xanthate moiety represents a photolabile linker. The photochemically released phenacyl radical fragments efficiently but reversibly add to the thiocarbonyl group of the parent xanthate molecule.
ER  -

TAZHE VEETIL, Aneesh; Tomáš ŠOLOMEK; Bokolombe Pitchou NGOY; Nela PAVLÍKOVÁ; Dominik HEGER a Petr KLÁN. Photochemistry of S-Phenacyl Xanthates. \textit{Journal of Organic Chemistry}. Columbus, OH, USA: the American Chemical Society, 2011, roč.~76, č.~20, s.~8232-8242. ISSN~0022-3263. Dostupné z: https://doi.org/10.1021/jo201385b.

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