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Stereoselective Stille coupling reactions of 1,1-bis(trialkylstannyl)ethenes

✍ Scribed by Peter Quayle; Jingyang Wang; Jie Xu; Christopher J. Urch

Book ID: 104258521
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 230 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10583-4

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✦ Synopsis

Stille coupling of l,l-bis(tri-n-butyistannyl)ethenes proceeds in a stereoselective manner to afford the E-vinylstannanes. Repetition of this sequence affords a new route to tri-substituted alkenes. Intramoleeular Stille coupling of a suitable vin~l bromide affords a pyrmlyl-derived vinylstannane. In certain cases, with bulky electrophiles, butyl migration rather than that of the sp 2-hybridised cenlxe is observed. A working model is put forward in order to rationalise these results.

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