TY  - JOUR
A1  - Mai-Linde, Yasemin
A1  - Linker, Torsten
T1  - Radical clock probes to determine carbohydrate radical stabilities
JF  - Organic letters
N2  - Carbohydrate radical stabilities in the 1- and 2-position have been determined by a radical clock approach, starting from cyclopropanated sugars with xanthates as precursors. Various hexoses and pentoses afforded 1-deoxy sugars as main products, indicating that anomeric radicals are more stable than radicals in the 2-position. An additional influence of the configurations on radical stabilities has been observed. Our results should be interesting for the understanding of 1,2-radical rearrangements in carbohydrate chemistry and offer an easy access to deoxy-vinyl sugars.
KW  - stereoselective-synthesis
KW  - convenient synthesis
KW  - chemistry
KW  - cyclopropanation
KW  - mechanism
KW  - glycals
KW  - beta-(acyloxy)alkylrear
KW  - rangement
KW  - sugars
Y1  - 2020
U6  - https://doi.org/10.1021/acs.orglett.0c00111
SN  - 1523-7060
SN  - 1523-7052
VL  - 22
IS  - 4
SP  - 1525
EP  - 1529
PB  - American Chemical Society
CY  - Washington
ER  - 
TY  - GEN
A1  - Schmidt, Bernd
A1  - Elizarov, Nelli
A1  - Berger, René
A1  - Hölter, Frank
T1  - Scope and limitations of the Heck–Matsuda-coupling of phenol diazonium salts and styrenes
BT  - a protecting-group economic synthesis of phenolic stilbenes
N2  - 4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4’-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior.
T3  - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - 242 
KW  - catalyzed cross metathesis
KW  - o bond formation
KW  - arenediazonium salts
KW  - stereoselective-synthesis
KW  - arylboronic acids
KW  - substituted stilbenes
KW  - aryldiazonium salts
KW  - palladium catalyst
KW  - trans-stilbenes
KW  - boronic acid
Y1  - 2013
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:517-opus4-95070
SP  - 3674
EP  - 3691
ER  -