[13686-66-3]  · C6H17NSi  · N,N-Diethylaminodimethylsilane  · (MW 131.29)

(reagent for intramolecular hydrosilation of allyl alcohols1 and intermolecular hydrosilation of 1,7-diynes2)

Physical Data: bp 112 °C/760 mmHg; n20D 1.4087; d204 mr3000.7505 g cm-3.

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.

Intramolecular Hydrosilation Agent.

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

Hydrosilation Agent.

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

1. Tamao, K.; Nakagawa, Y.; Ito, Y. OM 1993, 12, 2297.
2. Tamao, K.; Kobayashi, K.; Ito, Y. JACS 1989, 111, 6478.

Kohei Tamao

Kyoto University, Japan

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