Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 11
74
Views
1
CrossRef citations to date
0
Altmetric
Original Articles

Diethylaluminum Chloride Mediated Vinylsilane Synthesis: Comparison of Different Solvent Systems

, , , , &
Pages 1943-1950 | Received 03 Jan 2004, Published online: 20 Aug 2006

References

  • Blumenkopf , T. A. and Overman , L. E. 1986 . Vinylsilane‐ and alkynylsilane‐terminated cyclization reactions . Chem. Rev. , 86 : 857
  • Colvin , E. W. 1981 . Silicon in Organic Synthesis London : Butterworths .
  • Benkes , R. F. , Dunny , S. , Jones , P. R. and Nerlekar , P. G. 1967 . The formation of 1,6‐bis(trichlorosilyl)hexane by the chloroplatinic acid catalyzed hydrosilylation of 1‐hexyne . J. Org. Chem. , 32 : 2634
  • Weber , W. P. , Willard , A. K. and Boettger , H. G. 1971 . Mass spectroscopy of organosilicon compounds. Examples of interaction of the silyl center with remote phenyl groups . J. Org. Chem. , 36 : 1620
  • Miller , R. B. and Reichenbach , T. 1974 . The stereospecific synthesis of vinyl valides using a vinylsilane as the synthetic precursor . Tetrahedron Lett. , : 543 [CROSSREF]
  • Zweifel , G. and On , H. P. 1980 . A convenient route to (E)‐1‐alkenylsilanes via isomerization of (Z)‐1‐alkenylsilanes . Synthesis , : 803 [CROSSREF]
  • Koerwitz , F. L. , Hammound , G. B. and Wiemer , D. F. 1989 . Synthesis of vinyl silanes from vinyl silane phosphates . J. Org. Chem. , 54 : 743
  • Bates , T. F. and Thomas , R. D. 1989 . A new alkyllithium reagent for the direct conversion of aldehydes and ketones to vinylsilanes . J. Org. Chem. , 54 : 1784
  • Ni , Z.‐J. , Yang , P.‐F. , Ng , D. K.P. , Tzeng , Y.‐L. and Luh , T.‐Y. 1990 . Unified synthesis of vinylsilanes and silylated butadienes. Nickel‐catalyzed olefination and silylolefination of dithioacetals . J. Am. Chem. Soc. , 112 : 9356
  • Taylor , R. T. , Degenhardt , C. R. , Melega , W. P. and Paquette , L. A. 1977 . Direct conversion of ketones to vinylsilanes, ‐germanes, and ‐stannanes . Tetrahedron Lett. , 2 : 159 [CROSSREF]
  • Chan , T. H. , Baldassare , A. and Massuda , D. 1976 . Synthesis of vinylsilanes from benzenesulfonylhydrazones . Synthesis , : 801 [CROSSREF]
  • Petasis , N. A. and Akritopoulou , I. 1992 . Titanium‐mediated carbonyl olefinations; 3: conversion of carbonyl compounds to vinylsilanes with cyclopentadienyl(trimethylsilylmethyl)titanium(IV) derivatives . Synlett. , 8 : 665 [CROSSREF]
  • Gröbel , B.‐TH. and Seebach , D. 1977 . Erzeugung von und Olefinierung mit α‐S, ‐Se‐, ‐Si‐ und ‐Sn‐ perheterosubstituierten (Trimethylsilyl)methyllithium‐Verbindungen . Chem. Ber. , 110 : 852
  • Itami , K. , Nokami , T. and Yoshida , J.‐I. 2000 . [bis(2‐Pyridyldimethylsilyl)methyl]lithium. New reagent for the stereoselective synthesis of vinylsilanes . Org. Lett. , 2 : 1299 [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Plénat , F. 1981 . New synthesis of alcadien‐1,3 yl phosphonium salts . Tetrahedron Lett. , 22 : 4705 [CROSSREF]
  • Gilman , H. and Tomasi , R. A. 1962 . α‐Silyl‐substituted ylides. Tetraphenylallene via the Wittig reaction . J. Org. Chem. , 27 : 3647
  • Kwan , M. L. , Yeung , C. W. , Breno , K. L. and Doxsee , K. M. 2001 . Stereoselective one‐pot synthesis of vinylsilanes from aromatic aldehydes . Tetrahedron Lett. , 42 : 1411 [CROSSREF]
  • Peterson , D. J. 1968 . A carbonyl olefination reaction using silyl‐substituted organometallic compounds . J. Org. Chem. , 33 : 780
  • Kwan , M. L. and Battiste , M. A. 2002 . A convenient one‐pot organoaluminum mediated vinylsilane synthesis from non‐enolizable ketones via the peterson protocol . Tetrahedron Lett. , 43 : 8765 [CROSSREF]
  • Roesky , H. W. , Storr , J. , Klemp , A. , Schmidt , H.‐G. , Noltemeyer , M. , Fleischer , R. and Stalke , D. 1996 . Hydrolysis of trimesitylgallium and trimesitylaluminum: structures along a reaction pathway . J. Am. Chem. Soc. , 118 : 1380 [CROSSREF]
  • Pasynkiewicz , S. 1990 . Alumoxanes—synthesis, structures, complexes and reactions . Polyhedron , 9 : 429 [CROSSREF]

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.