Abstract
The addition of aminostannanes to a variety of di-substituted acetylenes and ethylenes is reported; leading to a wide range of functionally-substituted organotin compounds. It has been demonstrated that R 3SnNMe 2 (where R = Me or Et) adds to diethyl acetylenedicarboxylate, 1-chloro-2-phenylacetylene, and substituted ethylenes of the type RCHCR′R″ (where R and R′ = H and/or Me; and R″ = CN, CHO, or COOMe). Similarly, it is shown that the less reactive Me 3SiNMe 2 and Me 3GeNMe 2 will also add to diethyl acetylenedicarboxylate. The aminostannylation of nitrosobenzene, ethyl isothiocyanate, and tetracyanoethylene are also presented. Of particular interest is the formation of p-CH 3C 6H 4NC(SnMe 3)NMe 2 from Me 3SnNMe 2 and p-CH 3C 6H 4NC; this represents the first example of a 1,1-insertion reaction of an unsaturated substrate outside transition metal chemistry. An attempt is made to elucidate the structures by spectra and by comparison with similar systems.
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