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N-methyl-N-anilinomethyl diphenylphosphine oxide: a versatile reagent for the synthesis of enamines

✍ Scribed by N.L.J.M. Broekhof; F.L. Jonkers; A. van der Gen

Publisher
Elsevier Science
Year
1980
Tongue
French
Weight
212 KB
Volume
21
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cyclic as well as acyclic ketones, both saturated and a,b-unsaturated, can be converted into their homologous enamines by Horner-Wittig reaction with g-methyl-L-anilinomethyl diphenylphosphine oxide (3).

Enamines are highly valued intermediates in organic synthesis. They react with a large variety of electrophiles to give, after hydrolysis, a-substituted carbonyl compounds.l

We have recently reported that aromatic as well as aliphatic and a,&unsaturated aldehydes can be converted into their homologous enamines 2 in excellent yields (75-95%) by Horner-Wittig reaction with N-morpholinomethyl diphenylphosphine oxide.2 -

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