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K. Narasaka*, H. Kusama, Y. Hayashi (1992)
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AIBN‐initiated radical reactions of 5‐membered cyclic xanthates, 1,3‐oxathiolane‐2‐thiones, with tributyltin hydride are described. Alkenes are formed at 0.025 M concentration of tributyltin hydride, whereas a higher concentration (0.25 M) gives 1,3‐oxathiolanes. A mixture of alkene and 1,3‐oxathiolane is obtained by use of intermediate concentrations. Reactions of cis‐and trans‐4,5‐dialkyl‐1,3‐oxathiolane‐2‐thiones with tributyltin hydride afford E‐alkenes stereoselectively. For an application of this alkene formation reaction, geraniol has been converted to linalool silyl ether in good yield.
Heteroatom Chemistry – Wiley
Published: Jan 1, 1995
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