[13686-66-3] · C6H17NSi · N,N-Diethylaminodimethylsilane · (MW 131.29)
Physical Data: bp 112 °C/760 mmHg; n
Solubility: sol common aprotic organic solvents.
Preparative Method: by treatment of commercially available Chlorodimethylsilane (ClMe2SiH) and diethylamine in the presence of triethylamine in ether, followed by filtration and distillation.
Handling, Storage, and Precautions: moisture sensitive and corrosive. Must be stored under nitrogen in a tightly capped bottle in a freezer and transferred or weighed quickly via syringe. Use in a fume hood.
For a detailed description of the intramolecular hydrosilation procedure, see 1,1,3,3-Tetramethyldisilazane. N,N-Diethylaminodimethylsilane is a useful reagent for the conversion of hydroxy groups of allyl or homoallyl alcohols into hydrodimethylsilyl ethers for use in intramolecular hydrosilation reactions. In some cases, N,N-diethylaminodimethylsilane gives superior results compared to the more commonly employed 1,1,3,3-tetramethyldisilazane (eq 1).1
Another application of this difunctional hydrosilane is in the nickel-catalyzed hydrosilation of 1,7-octadiyne, which affords a 1,2-dialkylidenecyclohexane with a (Z)-vinylsilane moiety. This exocyclic silyl diene is treated with an allyl alcohol to give a silicon-tethered triene that undergoes intramolecular Diels-Alder reaction and subsequent oxidative cleavage of the silicon-carbon bond to afford a bicyclic diol (eq 2).2
Kyoto University, Japan