Ketone To Vinyl Iodide

Tetrahedron letters 1991 32 44 6449 6452.

Ketone to vinyl iodide. 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 corresponding gem dihalides. The halogenation proceeded smoothly under mild conditions. Please select more than one item to compare. When water is present the reaction product can revert to the ketone.

Some famous vinyl iodide synthesis methods involve conversion of aldehyde or ketone to vinyl iodide. The addition of hi to the double bond is not rate controlling but it may be shown that the rate of formation of 1 iodo 3 butanone is more rapid than that for 2 iodo 3 butanone. When the reaction site is not sterically hindered a second iodide can recombine to form the geminal di iodide. Tatsuo ishiyama norio miyaura akira suzuki.

Iso as a 6 8 to 1 mixture of f and z isomws. A general method for the preparation of vinyl iodides from ketones involves the treatment of the hydrazone of the ketone with 2 equivalents of iodine in diethyl ether in the presence of excess triethylamine 3 in addition to the vinyl iodide one often also obtains varying amounts of the geminal diiodide which can frequently be converted into the desired vinyl iodide upon treatment with strong base. 3 we now wish to report a novel rearrangement of the hydrazone of a bicyclic enone which. Search results for magnesium iodide at sigma aldrich.

2436 in summary high yields of vinyl iodides be obtained from various ketones as well as some b keto carbonyl compounds via vinyl phosphate intermediates. 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. Then the hydrazone is converted to vinyl iodide by addition of iodide and dbu. The kinetics of the reaction of hydrogen iodide with methyl vinyl ketone were also measured.

Such chiral moieties are widespread in natural products and the development of. Select up to 4 products. A halide exchange reaction of vinyl bromides with potassium iodide proceeds smoothly in the presence of a copper catalyst under mild reaction conditions to provide the corresponding vinyl iodides stereospecifically and in good yields.