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Regiochemistry of reactions of α-alkoxyallylphosphine oxide ylides with electrophiles.

✍ Scribed by Mehran Maleki; J.Alien Miller; O.William Lever Jr.

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 212 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)82022-0

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✦ Synopsis

Anions 4, derived from u-methoxyallylphosphine oxides 3, react with electrophiles in a highly regioselective fashion to give products of u-attack or y-attack depending upon the substitution pattern of the ylid 4 and the nature of the electrophile. _

This elimination normally requires replacement of lithium by sodium or potassium, then heating; cf. Ref. 5.

To our knowledge this is the first report of such a synthetic operation. The corresponding phosphonates react only at the y-carbon: Ref. 7.

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