Ketone To Vinyl Iodide

Synthesis of vinyl iodides from ketones koo lee and david f wier department of chemistry university of iowa iowa city iowa 52242 abstract.

Ketone to vinyl iodide. Rate constants for the reaction over the temperature range 281 355 c fit the arrhenius equation. Chemical specialities hyderabad telangana. 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.

Vinyl iodides are versatile molecules that serve as important building blocks and precursors in organic synthesis. 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. 18531 94 7 offered by s. In organic chemistry a vinyl iodide also known as an iodoalkene functional group is an alkene with one or more iodide substituents.

Manufacturer of speciality chemicals tributylphosphine acid methyl iodide acid methyl vinyl ketone and r binol cas no. 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. 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. The unimolecular decomposition of 2 iodo 3 butanone to methyl vinyl ketone and hydrogen iodide was also measured in the same system.

15 2433 2436 1993 0040 4039 93 6 00 00 printed in great britain perganton press ltd the reaction of vinyl phosphates with iodotrimethylsilane. Ryu synlett 2007 59 62. The ketone necessary for the hydrazone to vinyl iodide transformation was then the enone 2. 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.

They are commonly used in carbon carbon forming reactions in transition metal catalyzed cross coupling reactions such as stille reaction heck.