J 2011

The Power of Solvent in Altering the Course of Photorearrangements

ŠEBEJ, Peter, Bum He LIM, Bong Ser PARK, Richard S. GIVENS, Petr KLÁN et. al.

Basic information

Original name

The Power of Solvent in Altering the Course of Photorearrangements

Name in Czech

Schopnost rozpouštědla měnit mechanismus fotochemického přesmyku

Authors

ŠEBEJ, Peter (703 Slovakia, belonging to the institution), Bum He LIM (410 Republic of Korea), Bong Ser PARK (410 Republic of Korea), Richard S. GIVENS (840 United States of America) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Organic Letters, Washington D.C., USA, American Chemical Society, 2011, 1523-7060

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 5.862

RIV identification code

RIV/00216224:14310/11:00052645

Organization unit

Faculty of Science

DOI

UT WoS

000287122800026

Keywords (in Czech)

Fotochemi; foto-Favorskéheho přesmyk; voda

Keywords in English

Photochemistry; photo-Favorskii rearrangement; water

Tags

Tags

International impact, Reviewed
Změněno: 1/4/2015 22:21, prof. RNDr. Petr Klán, Ph.D.

Abstract

V originále

A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzofuranones occurs abruptly at low water concentrations (~8%). The surprisingly clean yields suggest that such reactions are synthetically promising.

Links

ED0001/01/01, research and development project
Name: CETOCOEN
ME09021, research and development project
Name: Vývoj nových fotoaktivovatelných systémů pro biologické studie
Investor: Ministry of Education, Youth and Sports of the CR, New photoactivatable systems for biological studies, Research and Development Programme KONTAKT (ME)
MSM0021622413, plan (intention)
Name: Proteiny v metabolismu a při interakci organismů s prostředím
Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment
MUNI/A/0980/2009, interní kód MU
Name: Molekulární a supramolekulární stavební bloky pro nanostrukturované materiály (Acronym: MOSTNAMAT)
Investor: Masaryk University, Category A