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 (356 Indie, domácí), Tomáš ŠOLOMEK (703 Slovensko, domácí), Bokolombe Pitchou NGOY (180 Konžská demokratická republika, domácí), Nela PAVLÍKOVÁ (203 Česká republika, domácí), Dominik HEGER (203 Česká republika, domácí) a Petr KLÁN (203 Česká republika, garant, domácí)

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

Kód RIV

RIV/00216224:14310/11:00050098

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.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://dx.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 = {http://dx.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://dx.doi.org/10.1021/jo201385b.

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