| Identification | Back Directory | [Name]
1,2-Diethoxy-1,2-bis(trimethylsilyloxy)ethylene | [CAS]
90054-58-3 | [Synonyms]
1,2-Diethoxy-1,2-bis(trimethylsilyloxy)ethylene
3,6-Dioxa-2,7-disilaoct-4-ene, 4,5-diethoxy-2,2,7,7-tetramethyl- | [Molecular Formula]
C12H28O4Si2 | [MDL Number]
MFCD17013250 | [MOL File]
90054-58-3.mol | [Molecular Weight]
292.52 |
| Hazard Information | Back Directory | [Physical properties]
bp 68–70°C/5 mmHg. | [Uses]
1,2-Diethoxy-1,2-bis(trimethylsilyloxy)-
ethylene is used in synthetic equivalent of the acyl anion C(O)CO2Et; useful in
ZnCl2-mediated nucleophilic additions to aldehydes and ketones,
Michael additions to enones,and substitution reactions of
SN1-active alkyl halides1 and carboxylic acid chlorides.
| [Preparation]
can be prepared in one step from diethyl
oxalate using the R¨1hlmann version of the acyloin condensation
(eq 1).Although a yield of 64% of isolated product was
reported,this could not be reproduced in a careful series of
experiments.Rather, yields of 21¨C25% are consistently obtained
(0.1¨C1.0 molar scale).The product consists of a (Z/E)
isomeric mixture which is of no consequence for synthetic applications.
| [Precautions]
Somewhat air and moisture sensitive and should therefore be handled and stored under an atmosphere of an inert gas such as N2 and in nonprotic solvents. Use in a fume hood.
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