4-Haloalkyoxytributyltin compounds are relatively unstable and on heating give the corresponding tetrahydrofuran compounds in quantitative amounts. The 5-haloalkoxytributyltin compounds are more stable but at higher temperatures they also decompose quantitatively to tetrahydropyran compounds.
Tri-n-butyltin ω-haloalkoxides are useful reagents for the preparation of sulfur-containing five and six-membered cyclic compounds combined with isothiocyanates.
Control of Product in the Reaction of Tributyltin ω-Haloalkoxide (<i>n</i>-Bu<sub>3</sub>SnO(CH<sub>2</sub>)<i><sub>n</sub></i>X) with Diphenylketene
作者:Ikuya Shibata、Akio Baba、Haruo Matsuda
DOI:10.1246/bcsj.59.4000
日期:1986.12
The reaction of tributyltin ω-haloalkoxide with diphenylketene gave cyclic ketene acetals and/or lactones, and the ratio of these products were controled by the number of methylene groups and by the addition of Lewis base in the reaction system. Moreover, the direct cycloaddition of diphenylketene with cyclic ethers proceeded in high yields, catalyzed by organotin halide–Lewis base complexes.