Azidosilanes trimethylsilyl azide

Reactions of 59 with less hindered azides can be more complex. With trimethylsilyl azide, the isolated product was the azidosilane 73. The formation of 73 can be rationalized, however, as proceeding through the initial formation of a silanimine, followed by addition of MesSi—N3 across the Si=N double bond, as shown in equation 110. When 59 was treated with 1-adamantyl azide, the product was the silatetrazoline 74. Once again this product may have resulted from initial formation of a silanimine, followed in this case by 2 + 3 cycloaddition of the azide to the Si=N double bond (equation 111)98 148. 

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