Journal of Organic Chemistry p. 1061 - 1067 (1981)
Update date:2022-08-16
Topics:
Patel, Babu A.
Kim, Jin-Il I.
Bender, Diana D.
Kao, Lien-Chung
Heck, Richard F.
A variety of vinylic halides has been found to react with acrolein or methacrolein acetals and amines with palladium catalysts to form 5-amino 3-enal acetals and/or dienal acetals.The reaction products yield 2,4-dienals on treatment with aqueous acids, in moderate to good yields.Crotonaldehyde dimethyl acetal also undergoes the reaction, but only in low yields. 3-Buten-2-one ethylene ketal reacted well under the same conditions, however, and Hofmann elimination and hydrolysis of the product amine gave (E,E)-3,5-heptadien-2-one in 90percent yield.
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