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Synthesis of vinyl ethers by homologation of aldehydes via radical reductive elimination

โœ Scribed by Jean-Michel Vatele

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
224 KB
Volume
25
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Methoxyphenylthiomethyllithium 1 reacts with aldehydes to give adducts which are then transformed into xanthates. These compounds, by reaction with tri-n-butylstannane, afford vinyl ethers in good yields. Vinyl ethers, long time regarded simply as derivatives of aldehydes and ketones, are now considered, since the discovery of their abilities to act as electron-rich olefins in 2+2 cycloadditions 1 and to form either ally12 or vinyl 3 anions, a useful class of compounds. The stereo-and regioselectivity of these reactions depends, among other factors, on the geometry of the double bond of the vinyl ether. While several methods 4-10 exist to achieve the transformation of aldehydes into vinyl ethers, most of them based upon the Wittig reaction4'5 or a modification thereof, 6,7 none of them is stereoselective and they give mixtures of Z-and E-isomers.

๐Ÿ“œ SIMILAR VOLUMES

Synthesis of vinylic and cyclic sulfones
Synthesis of vinylic and cyclic sulfones via a radical addition-elimination sequence
โœ Albert Padwa; S.Shaun Murphree; Philip E. Yeske ๐Ÿ“‚ Article ๐Ÿ“… 1990 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 253 KB

Radical attack on the double bond of 2,3-bis(phenylsulfonyl)-1 -propene leads to an intermediate sulfonyl stabilized radical. This species readily fragments to produce a new vinyl sulfone which can undergo further radical cyclization to give a six ring sulfone.