SYNTHESIS OF (AMINOMETHYL)SILANES WITH THE USE OF AN EASILY CLEAVABLE CARBON-SILICON BOND

A number of (chloromethyl)dimethylsilanes 8a-c bearing a heterocyclic substituent (ClCH2)(CH3)2Si(C4HnX) (a, n = 3, X = 0; b, n = 3, X = S; c, n = 5, X = 0) were synthesized and aminated with morpholine to give (aminomethyl)silanes 9a-c (C5H10NO)(CH3)2Si(C4HnX) (a, n = 3, X = 0; b, n = 3, X = S; c, n = 5, X = 0). They were screened for their capacity to undergo nucleophilic substitution reactions using lithium aluminum hydride. The heterocyclic substituent on silane 9c was easily replaced with hydride, alkyls, and the trimethylsilyl group. This series of reactions was successfully applied to the synthesis of the pentamethyldisilane 14 (C5H10NO)(CH3)5Si2 and the acetylene (aminomethyl)silane 21 (C13H19NSi) not readily available in pure form by other means.