ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
On the Rearrangement of Li Alkoxides from Dichloromethyllithium and Carbonyl Compounds into α-Chlorooxiranes and α-ChloroaldehydesThe Li alkoxides 2, formed from dichloromethyllithium and carbonyl compounds, yield the alkohols 3 (table 1) and the silyl ethers 4 (table 2) on protolysis and treatment with trimethyl-chlorosilane, respectively. The ability of the Li alkoxides 2 to rearrange (at 80-90°C) into α-chlorooxiranes or α-chloroaldehydes is significantly influenced by steric as well as electronic substituent effects. A mechanistic interpretation of the experimental results is given.
Notes:
Die Addition von Dichlormethyllithium an Carbonylverbindungen ergibt die Li-Alkoxide 2, deren Protolyse die Alkohole 3 (Tab. 1) und deren Trimethylsilylierung die Silyläther 4 (Tab. 2) liefert. Die Bereitschaft der Li-Alkoxide 2 zur Umlagerung in α-Chloroxirane bzw. α-Chloraldehyde (bei 80-90°C) hängt yon sterischen und elektronischen Substituenten-einflüssen ab. Die experimentellen Ergebnisse werden mechanistisch interpretiert.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19731060824
