Ketone To Vinyl Iodide

15 2433 2436 1993 0040 4039 93 6 00 00 printed in great britain perganton press ltd the reaction of vinyl phosphates with iodotrimethylsilane.

Ketone to vinyl iodide.

We considered using in situ generated vinyl boron ate complexes vi derived from enantioenriched boronic esters v and vinyllithium in a radical polar crossover reaction with various alkyl iodides and report herein that this key transformation followed by oxidation offers a new route to α chiral ketones. Chemical specialities hyderabad telangana. Various ketones as the electrophiles react in a one pot three component coupling with an aluminum allenoate intermediate derived from ethyl propiolate and alluminium iodide to yield β iodo morita baylis hillman adducts with high yield and excellent z stereoselectivity. Such chiral moieties are widespread in natural products and the development of.

Ryu synlett 2007 59 62. A new method for preparation of vinyl iodides from ketones is described. Application of pho 3 p halogen based reagents allows the preparation of vinyl halides in good to excellent yields from enolizable ketones whereas aldehydes afforded the. Vinyl iodides are versatile molecules that serve as important building blocks and precursors in organic synthesis.

18531 94 7 offered by s. This reaction is relatively slow compared to the formation of the above equilibrium. In organic chemistry a vinyl iodide also known as an iodoalkene functional group is an alkene with one or more iodide substituents. The use of catalytic amounts of copper iodide and trans n n dimethylcyclohexane 1 2 diamine in the presence of tetramethylammonium chloride or.

Rate constants for the reaction over the temperature range 281 355 c fit the arrhenius equation. Synthesis of vinyl iodides from ketones koo lee and david f wier department of chemistry university of iowa iowa city iowa 52242 abstract. This optically active enone 2 was prepared in 7 steps from optically active wieland miescher ketone 1 5 6 the hydrazone 3 was prepared by treatment of racemic 2 with hydrazine hydrochloride in ethanol in 9896 yield. The ketone necessary for the hydrazone to vinyl iodide transformation was then the enone 2.

Hydrazone iodination is an organic reaction in which a hydrazone is converted into a vinyl iodide by reaction of iodine and a non nucleophilic base such as dbu first published by derek barton in 1962 the reaction is sometimes referred to as the barton reaction although there are many different barton reactions or more descriptively as the barton vinyl iodine procedure.