90252-81-6Relevant articles and documents
Studies on Ketene and Its Derivatives. CXVIII. Nickel- or Palladium-Catalyzed Reaction of Diketene with Organometallics. Synthesis of 3-Substituted 3-Butenoic Acids
Abe, Yoshihito,Sato, Masayuki,Goto, Hiroyuki,Sugawara, Rie,Takahashi, Eri,Kato, Tetsuzo
, p. 4346 - 4354 (2007/10/02)
The reaction of diketene (1) with some organometallics was investigated.The reaction of 1 with benzyl Grignard reagents in the presence of nickel(II) chloride afforded 3-benzyl-3-butenoic acids 2a-e.In the presence of dichloronickel, primary alkylmagnesium bromides reacted with 1 to give 3-methylenealkanoic acids 2g-i. (E)-1-Alkenyldiisobutylaluminiums, in the presence of Pd(O)-catalyst, reacted with 1 to give 3-methylene-4-alkenoic acids 5a-c.Similarly, alkynyl- and aryl-zinc chlorides gave 3-methylene-4-alkynoic acids 7a-d and 3-aryl-3-butenoic acids 8a-c, respectively.Keywords - diketene: Grignard reagent; alkenylaluminium; alkynylzinc chloride; arylzinc chloride; palladium-catalyst; nickel-catalyst; 3-butenoic acid; 3-substituted 3-butenoic acid