141694-60-2Relevant academic research and scientific papers
A new approach towards the synthesis of sp3 1,1-diiodoalkanes
Aufauvre, Lionel,Knochel, Paul,Marek, Ilan
, p. 2207 - 2208 (1999)
An easy and straightforward method for the synthesis of gem-diiodo derivatives is reported.
Practical Procedures for the Preparation of N-tert-Butyldimethylsilylhydrazones and Their Use in Modified Wolff-Kishner Reductions and in the Synthesis of Vinyl Halides and gem-Dihalides
Furrow, Michael E.,Myers, Andrew G.
, p. 5436 - 5445 (2007/10/03)
In this work we develop practical chemistry for the preparation of N-tert-butyldimethylsilylhydrazone (TBSH) derivatives from carbonyl-containing compounds and show that these products serve as superior alternatives to simple hydrazones in Wolff-Kishner-type reduction reactions, in the Barton vinyl iodide preparation, in the synthesis of vinyl bromides, and in the synthesis of gem-diiodides, gem-dibromides, and gem-dichlorides. In our new procedure for silyl hydrazone synthesis, aliphatic and aromatic ketones and aldehydes are shown to undergo highly efficient coupling (typically >95% yield) to form the corresponding TBSH derivatives when combined with equimolar amounts of 1,2-bis(tert-butyldimethylsilyl)-hydrazine (BTBSH) and a catalytic quantity of scandium trifluoromethanesulfonate (typically, 0.01 mol %), neat, or in solvent. Optimized procedures are provided for the use of TBSH derivatives in a Wolff-Kishner-type reduction protocol that proceeds at low temperature (23-100 °C) and in a single reaction flask. Similarly, protocols for the use of TBSH derivatives as precursors to vinyl halides and gem-dihalides are described in detail.
Carbocupration/zinc carbenoid homologation and β-elimination reactions for a new synthesis of allenes - Application to the enantioselective synthesis of chiral allenes by deracemization of sp3-organometallic derivatives
Varghese, Jos P.,Zouev, Irena,Aufauvre, Lionel,Knochel, Paul,Marek, Ilan
, p. 4151 - 4158 (2007/10/03)
A new and straightforward carbocupration/zinc homologation/β-elimination reaction sequence allows the one-pot synthesis of polysubstituted allenes from acetylenic sulfoxides in excellent isolated chemical yields. Secondary zinc carbenoids were used for the homologation reaction, and so a new synthesis of 1,1-diiodoalkanes is described. This methodology also allows the synthesis of chiral allenes through thermodynamic equilibration of secondary organometallic derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002.
A new Procedure for the Synthesis of (E)-1-iodo-1-alkenes
Martinez, A. Garcia,Alvarez, R. Martinez,Gonzalez, S. Martinez,Subramanian, L. R.,Conrad, M.
, p. 2043 - 2044 (2007/10/02)
(E)-1-iodo-1-alkenes 4 can be prepared stereoselectively from aldehydes 1 via IH-elimination of 1,1-di-iodoalkanes 3 with DBU. Key words: Vinyl iodide; diiodoalkane; elimination; stereoselectivity.
