Synthesis of a-aminostannanes

Stannanes 6, 9, 1, and 4 were reported previously by us. [1] The methodology uses Katritzky's benzotriazole chemistry to prepare 14, 15, and 17. [2,3] Displacement of the benzotriazolyl group with tributylstannyllithium proceeded smoothly. Compounds 18 and 8 are new to this paper, but were prepared by the same method. Tsunoda, et al., have also prepared 8 by a different route. [ 4]


1. Pearson, W. H.; Stevens, E. P. Synthesis 1994, 904. Go back to text.
2. Katritzky, A. R.; Yannakopoulou, K.; Lue, P.; Rasala, D.; Urogdi, L. J. Chem. Soc., Perkin Trans. 1 1989, 225.
3. Katritzky, A. R.; Pilarski, B.; Urogdi, L. Org. Prep. and Proc. 1989, 21, 135.
4. Tsunoda, T.; Fujiwara, K.; Yamamoto, Y.; Itô, S. Tetrahedron Lett. 1991, 32, 1975.
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1. Transmetalation of acyclic aminostannanes: Primary organolithiums can be formed, but secondary organolithiums cannot
2. Transmetalation of cyclic aminostannanes: Secondary organolithiums are formed
3. Hypotheses: Conformational effects (i.e., a kinetic problem) or thermodynamics may be responsible
4. These studies allow a ranking of the relative stabilities of organolithiums
5. How the aminostannanes were made. (THIS PAGE)