14399-53-2

Basic information

• Product Name: bis(iodomethyl)zinc
• Synonyms: zinc, bis(iodomethyl)-
• CAS NO: 14399-53-2
• Molecular Formula: C₂H₄I₂Zn
• Molecular Weight: 347.2711
• Mol File: 14399-53-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: bis(iodomethyl)zinc(CAS DataBase Reference)
• NIST Chemistry Reference: bis(iodomethyl)zinc(14399-53-2)
• EPA Substance Registry System: bis(iodomethyl)zinc(14399-53-2)

Safety Data

• Hazardous Substances Data: 14399-53-2(Hazardous Substances Data)

Upstream product

• 75-11-6 diiodomethane 
• 557-20-0 diethylzinc 

Downstream Products

• 4127-47-3 2,2,3,3-tetramethylcyclopropane 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 110659-58-0 (1R,2R)-1-hydroxymethyl-2-phenylcyclopropane 
• 178602-54-5 (1S,2R,1'S,2'R)-2,2'-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclopropyl 
• 141116-62-3 (S)-1-((3aS,8aR)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-methyl-3-phenyl-propan-1-one 
• 142096-79-5 (-)-(1R,2R)-2-(2-phenylethyl)cyclopropylmethanol 
• 142096-79-5 (+)-(1S,2S)-2-(2-phenylethyl)cyclopropylmethanol 
• 37904-41-9 2-(2,2-dimethylcyclopropyl)-1-phenylethane 

Relevant articles and documents

Enantioselective synthesis and structure revision of solandelactone E

The first total synthesis of solandelactone E has been achieved by a novel and convergent strategy that required 23 steps. The synthesis features a diastereoselective acetal-directed cyclopropanation of an electron-deficient diene, a Sharpless asymmetric dihydroxylation, and a [2,3]-sigmatropic rearrangement of a selenoxide intermediate. Copyright

Forming Stereogenic Centers in Acyclic Systems from Alkynes

The combined carbometalation/zinc homologation followed by reactions with α-heterosubstituted aldehydes and imines proceed through a chair-like transition structure with the substituent of the incoming aldehyde residue preferentially occupying a pseudo-axial position to avoid the two gauche interactions. The heteroatom in the axial position produces a chelated intermediate (and not a Cornforth-Evans transition structure for α-chloro aldehydes and imines) leading to a face differentiation in the allylation reaction. This method provides access to functionalized products in which three new carbon-carbon bonds and two to three stereogenic centers, including a quaternary one, were created in acyclic systems in a single-pot operation from simple alkynes. All-carbon quaternary stereocenter: The combined carbometalation/zinc homologation of alkynes followed by reactions with α-heterosubstituted aldehydes and imines provides access to functionalized acyclic adducts. These adducts obtained in a single-pot reaction have three new carbon-carbon bonds and two to three stereogenic centers, including a quaternary carbon stereocenter.

Solution and Solid-State Structure of the "Wittig-Furukawa" Cyclopropanation Reagent

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Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes

The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.