89029-62-9

Upstream product

• 507-25-5 carbon tetraiodide 
• 100-52-7 benzaldehyde 
• 3757-88-8 tributylstannylethynylbenzene 
• 536-74-3 phenylacetylene 
• 75-47-8 iodoform 
• 100-39-0 benzyl bromide 
• 153467-26-6 diethyl diiodomethylphosphonate 
• 29949-93-7 iodomethylenetriphenylphosphorane 
• 3020-28-8 (iodomethyl)triphenylphosphonium iodide 

Downstream Products

• 29443-54-7 1,1-diiodo-2-phenylethane 
• 101349-79-5 2-phenylvinyl iodide 
• 23429-37-0 1-methyl-4-(phenylbuta-1,3-diyn-1-yl)benzene 

Relevant academic research and scientific papers

1,1-Di-iodoalkenes from Aldehydes and Triphenylphosphine-Carbon Tetraiodide

The Wittig-like transformation of aliphatic and aromatic aldehydes into 1,1-di-iodoalkenes can be achieved with triphenylphosphine-carbon tetraiodide.

1-Alkynyltriazenes as Functional Analogues of Ynamides

The chemical reactivity of 1-alkynyltriazenes has been investigated and is found to parallel the reactivity of ynamides. The similarity in reactivity of these two classes of compounds is demonstrated by addition reactions with acids, by cycloaddition reactions with ketenes, tetracyanoethene, and cyclopropanes, as well as by intramolecular cyclization reactions. The presence of reactive triazene groups in the products enables subsequent transformations. Overall, our results suggest that 1-alkynyltriazenes should become valuable reagents in synthetic organic chemistry. Cut from the same cloth: 1-Alkynyltriazenes are activated alkynes with a reactivity profile similar to ynamides. A series of different reactions are employed to compare the reactivities of the two compound classes. The triazene functional group in the products facilitates unique subsequent transformations.

One-pot synthesis of telluroketene acetals and haloketene acetals using sp2 geminated hetero organobismetallic intermediates

A novel one-pot synthesis of 1,1-dihalo-1-alkenes and 1,1-bis(butyltelluro) -1-alkenes was developed from hydrozirconation of alkynylzinc bromide with Cp2Zr(H)Cl and subsequent capture of the Zn/Zr 1,1-heterodimetallo-1- alkene intermediates wi

One-pot synthesis of 1-iodoalkynes and trisubstituted alkenes from benzylic and allylic bromides

1-Iodoalkynes are formed in moderate to high yields from readily accessible benzylic and allylic alkyl bromides by a one-pot homologation/double elimination procedure with iodoform (CHI3). The developed conditions include facile purification and avoid the use of an excess of triphenylphosphine (PPh3), as described in classical Corey-Fuchs iodoalkynylation conditions. Replacing CHI3 with CHI2Cl allows the isolation of the corresponding gem-(Z)-chloro-(E)-iodoalkene in good yield and stereoselectivity. Moreover, the use of benzhydryl bromides as nucleophiles enables the synthesis of trisubstituted alkenes under similar reaction conditions.

Highly efficient two-step synthesis of C-sp3-centered geminal diiodides

(Chemical Equation Presented) Trisubstituted gem-diiodoalkenes of functionalized chains are efficiently reduced to the corresponding terminal geminal diiodides in high yields upon treatment with the diazene precursor, diethyl 4-(hydrazinosulfonyl)-benzyl phosphonate.

A simple and practical method for the stereoselective synthesis of (Z)-1-iodo-1-alkenes from 1,1-diiodo-1-alkenes

Treatment of the 1,1-diiodo-1-alkenes 8, prepared from the corresponding aldehydes with CI4/PPh3, with Zn-Cu/AcOH in THF-MeOH gave the (Z)-1-iodo-1-alkenes 9, selectively, in good yields.

Expedient synthesis of 1,1-diiodoalkenes

1,1-Diiodoalkenes 1 were readily prepared from carbonyl compounds 2 and diethyl diiodomethylphosphonate (3), generated in situ from commercial diethyl iodomethylphosphonate (4) or diethyl methylphosphonate (5). Starting from aldehydes, iodoacetylenes 6 co

Z-1-VINYLIODIDE DURCH WITTIG-REAKTION

A wide spectrum of Z-1-iodo-alkenes is available by Wittig reaction of iodomethylenetrimethylphosphorane with aldehydes.The formation of 1,1-diiodo-1-alkenes as byproducts is explained.

A Wittig-like Synthesis of 1,1-Di-iodoalkenes

The synthesis of 1,1-diiodoalkenes from aliphatic and aromatic aldehydes and triphenylphosphine-carbon tetraiodide is described.The reagent does not work with ketones.With aldehydes, yields are dependent on the electrophilicity of the carbonyl group.