- Facile synthesis of trisubstituted allenynes by phosphane-mediated deoxygenation of 2,4-pentadiyn-1-o1
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A facile method for the synthesis of trisubstituted allenynes has been, developed. The process involves phosphane-mediated deoxygenation of 2,4-pentadiyn-l-ol derivatives. A vari- ety of propargyl alcohols can be transformed into allenynes in moderate to good yields under mild reaction conditions.
- Jiang, Huanfeng,Wang, Wei,Yin, Biaolin,Liu, Weibing
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experimental part
p. 4450 - 4453
(2010/10/02)
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- Organometal-mediated synthesis of conjugated allenynes, allenediynes, vinylallenes and diallenes
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An extensive study of the reactivity of organometallic reagents R3M (R3 = 1-alkenyl, 1-alkynyl, 3-alken-1-ynyl, 1,3-alkadiynyl or 1,2-alkadienyl; M = Li, MgCl, ZnCl, Cu, Ag) towards R1R2C=C=CH-X (1) and R1R2C(X)-CCH (4) is described.High yields of R1R2C=C=CH=R3 (2) have been obtained by reaction of 1 (X = Br) with R3-M (M = MgCl, ZnCl or Cu1/2Li1/2) using Pd4 as catalyst.Similarly, pure 2 have been obtained by the Pd4-catalyzed reaction of 4 (X = Br, OAc, OS(O)Me, OSO2Me, OP(O)(OEt)2) with R3-M (M = MgCl, ZnCl, Zn1/2, Cu, Cu1/2Li1/2, Ag or Ag1/2Li1/2).In some reactions with R3-Cu, compounds 4 were cnverted into 2 in the absence of the palladium catalyst.
- Ruitenberg, K.,Kleijn, H.,Westmijze, H.,Meijer, J.,Vermeer, P.
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p. 405 - 409
(2007/10/02)
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- PALLADIUM(0)-PROMOTED SYNTHESIS OF FUNCTIONALLY SUBSTITUTED ALLENES BY MEANS OF ORGANOZINC COMPOUNDS
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The paper describes new routes to aryl-, vinyl-, and 1-alkynylallenes and to diallenes via Pd(PPh3)4-promoted reaction of propargylic or allenic halides with appropriate organozinc halides.Propargylic acetates are also suited to prepare such allenes.
- Ruitenberg, K.,Kleijn, H.,Elsevier, C. J.,Meijer, J.,Vermeer, P.
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p. 1451 - 1452
(2007/10/02)
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- ALLENYLCOPPER(I) COMPOUNDSl SUITABLE REAGENTS FOR THE SYNTHESIS OF ALLENYNES
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Allenylcopper(I) compounds react smoothly and highly regioselectively with 1-iodo-1-alkynes to give allenynes in excellent yields.
- Ruitenberg, K.,Meijer, J.,Bullee, R. J.,Vermeer, P.
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p. 267 - 271
(2007/10/02)
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