26305-83-9Relevant articles and documents
A novel biotinylated suicide inhibitor for directed molecular evolution of lipolytic enzymes
Deussen,Danielsen,Breinholt,Borchert
, p. 507 - 513 (2000)
A bifunctional activity label (8)Scheme 1Reagents and conditions: (i) Me3SiCl, Et3N, CH2Cl2/ether; (ii) (EtO)3P/reflux; (iii) H2SO4/acetone; (iv) 1. COCl2, 2. N-hydrox
Direct chlorination of alcohols with chlorodimethylsilane catalyzed by a gallium trichloride/tartrate system under neutral conditions
Yasuda, Makoto,Shimizu, Kenji,Yamasaki, Satoshi,Baba, Akio
supporting information; experimental part, p. 2790 - 2795 (2009/02/03)
The reaction of secondary alcohols 1 with chlorodimethylsilane (HSiMe 2Cl) proceeded in the presence of a catalytic amount of GaCl 3/diethyl tartrate to give the corresponding organic chlorides 3. In the catalytic cycle, the reaction of diethyl tartrate 4a with HSiMe 2Cl 2 gives the chlorosilyl ether 5 with generation of H2. Alcohol-exchange between the formed chlorosilyl ether 5 and the substrate alcohol 1 affords alkoxychlorosilane 6, which reacts with catalytic GaCl 3 to give the chlorinated product 3. The moderate Lewis acidity of GaCl3 facilitates chlorination. Strong Lewis acids did not give product due to excessive affinity for the oxy-functionalities. Although tertiary alcohols were chlorinated by this system even in the absence of diethyl tartrate, certain alcohols that are less likely to give carbocationic species were effectively chlorinated using the GaCl3/diethyl tartrate system. The Royal Society of Chemistry.