Palladium-catalyzed three carbon chain extension reactions with acrolein acetals. A convenient synthesis of conjugated dienals

BA Patel, JII Kim, DD Bender, LC Kao…

Index: Patel, Babu A.; Kim, Jin-Il I.; Bender, Diana D.; Kao, Lien-Chung; Heck, Richard F. Journal of Organic Chemistry, 1981 , vol. 46, # 6 p. 1061 - 1067

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Citation Number: 27

Abstract

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-end acetals and/or dienal acetals. The reaction products yield 2, Cdienals 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 ...