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Please login to access the full content or check if you have access via5.2.24.5.3 Variation 3: Using 1,3-Cycloadditions of Alkynylstannanes
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Crisp, G. T., Science of Synthesis, (2003) 5, 510.
1,3-Dipolar cycloaddition reactions of alkynyltrimethylsilanes with nitrile oxides give 3-substituted 5-(trimethylstannyl)isoxazoles 33 and 3,5-disubstituted 4-(trimethylstannyl)isoxazoles 32 in modest to good yields, depending on the substituents on the fulminates and on the alkyne (Scheme 13).[6] 3-Phenyl- and 3-(ethoxycarbonyl)-5-(trimethylstannyl)isoxazoles 33 are not stable towards attempted purification on silica gel and are destannylated to give the corresponding 3-substituted isoxazoles (R1 = Ph, EtOC(O) as 34). The 3,5-disubstituted 4-(trimethylstannyl)isoxazoles are formed regioselectively and these derivatives are stable on silica gel.
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References
[6] | Meeeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
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