Ketone To Vinyl Iodide

Ryu synlett 2007 59 62.

Ketone to vinyl iodide.

This reaction is relatively slow compared to the formation of the above equilibrium. 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. 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. 15 2433 2436 1993 0040 4039 93 6 00 00 printed in great britain perganton press ltd the reaction of vinyl phosphates with iodotrimethylsilane.

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. Vinyl iodides are versatile molecules that serve as important building blocks and precursors in organic synthesis. In organic chemistry a vinyl iodide also known as an iodoalkene functional group is an alkene with one or more iodide substituents. Rate constants for the reaction over the temperature range 281 355 c fit the arrhenius equation.

18531 94 7 offered by s. They are commonly used in carbon carbon forming reactions in transition metal catalyzed cross coupling reactions such as stille reaction heck. Chemical specialities hyderabad telangana. A new method for preparation of vinyl iodides from ketones is described.

The use of catalytic amounts of copper iodide and trans n n dimethylcyclohexane 1 2 diamine in the presence of tetramethylammonium chloride or. The ketone necessary for the hydrazone to vinyl iodide transformation was then the enone 2. Such chiral moieties are widespread in natural products and the development of. 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.

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.