Protonation of acyllithium reagents by dichloromethane and dichloroarylmethane. A new method for the synthesis of {alpha},{alpha}-dichloro alcohols

Kabalka, G W; Li, N S; Yu, S

doi:10.1021/om00004a008

Title: Protonation of acyllithium reagents by dichloromethane and dichloroarylmethane. A new method for the synthesis of {alpha},{alpha}-dichloro alcohols

Full Record
Other Related Research

Abstract

The first example of the protonation of acylithium reagents by dichloromethane and dichloroarylmethane is described. The reaction affords the corresponding {alpha},{alpha}-dichloro alcohols in excellent yields. 23 refs., 1 tab.

Authors:

Kabalka, G W; Li, N S; Yu, S ^[1]

Univ. of Tennessee, Knoxville, TN (United States)

Publication Date:: Sat Apr 01 00:00:00 EST 1995

Sponsoring Org.:: USDOE

OSTI Identifier:: 81421

Resource Type:: Journal Article

Journal Name:: Organometallics

Additional Journal Information:: Journal Volume: 14; Journal Issue: 4; Other Information: PBD: Apr 1995

Country of Publication:: United States

Language:: English

Subject:: 40 CHEMISTRY; 99 MATHEMATICS, COMPUTERS, INFORMATION SCIENCE, MANAGEMENT, LAW, MISCELLANEOUS; ALCOHOLS; SYNTHESIS; ORGANOMETALLIC COMPOUNDS; CARBONYLATION; METHYLENE CHLORIDE; CARBON MONOXIDE; NUMERICAL DATA; REAGENTS

Citation Formats


                    Kabalka, G W, Li, N S, and Yu, S. Protonation of acyllithium reagents by dichloromethane and dichloroarylmethane. A new method for the synthesis of {alpha},{alpha}-dichloro alcohols.  United States: N. p., 1995. 
        Web.  doi:10.1021/om00004a008.

Copy to clipboard


                    Kabalka, G W, Li, N S, & Yu, S. Protonation of acyllithium reagents by dichloromethane and dichloroarylmethane. A new method for the synthesis of {alpha},{alpha}-dichloro alcohols.  United States.  https://doi.org/10.1021/om00004a008

Copy to clipboard


                    Kabalka, G W, Li, N S, and Yu, S. 1995.  
        "Protonation of acyllithium reagents by dichloromethane and dichloroarylmethane. A new method for the synthesis of {alpha},{alpha}-dichloro alcohols".  United States.  https://doi.org/10.1021/om00004a008.

Copy to clipboard


                    
@article{osti_81421,

  title        = {Protonation of acyllithium reagents by dichloromethane and dichloroarylmethane. A new method for the synthesis of {alpha},{alpha}-dichloro alcohols},

  author       = {Kabalka, G W and Li, N S and Yu, S},

  abstractNote = {The first example of the protonation of acylithium reagents by dichloromethane and dichloroarylmethane is described. The reaction affords the corresponding {alpha},{alpha}-dichloro alcohols in excellent yields. 23 refs., 1 tab.},

  doi          = {10.1021/om00004a008},

  url          = {https://www.osti.gov/biblio/81421},
  journal      = {Organometallics},
number       = 4,

  volume       = 14,

  place        = {United States},

  year         = {Sat Apr 01 00:00:00 EST 1995},

  month        = {Sat Apr 01 00:00:00 EST 1995}

}

Copy to clipboard

Journal Article:

https://doi.org/10.1021/om00004a008

Other availability

Find in Google Scholar

Search WorldCat to find libraries that may hold this journal

Save / Share:

Export Metadata

Save to My Library

Similar records in OSTI.GOV collections:

Protonation of acyllithium reagents by acetonitrile: Synthesis of {beta}-hydroxy nitriles

Journal Article Li, Nan-Sheng; Yu, Su; Kabalka, G - Journal of Organic Chemistry

In recent years, the reaction of electrophiles with acyllithium (RCOLi) reagents has been extensively studied and has proven to be a convenient route to acylated products. For example, Seyferth reported that acyllithium reagents, generated in situ from an alkyllithium and carbon monoxide at -110 {degrees}C to -135 {degrees}C, would react with aldehydes, ketones, esters, lactones, isocyanates, isothiocyanates, carbodiimides, carbon disulfide, carbonyl sulfide, organic disulfides, iron pentacarbonyl, and trimethylchlorosilane to give acylated products. Nudelman found that the acyllithium generated from phenyllithium in the presence of alkyl bromides gave diphenylalkylcarbinols. The authors recently reported that trialkylboranes reacted with acyllithium reagents to affordmore »« less
https://doi.org/10.1021/jo00123a042
Application of (. alpha. -phosphonoacyl)silane reagents to the synthesis of. alpha. -. beta. -unsaturated acylsilanes

Journal Article Nowick, J; Danheiser, R - Journal of Organic Chemistry; (USA)

An efficient and convergent synthetic route to {alpha},{beta}-unsaturated acylsilanes has been developed based on the Horner-Wadsworth-Emmons reaction of ({alpha}-phosphonoacyl)silanes. The Arbuzov reaction of the ({alpha}-iodoacyl)silane 1c with trimethyl phosphite provides access to the phosphonate 2, which can be alkylated by treatment with potassium tert-butoxide and methyl iodide to afford 3. These ({alpha}-phosphonacyl)silane reagents combine smoothly with a variety of aldehydes to furnish {alpha},{beta}-unsaturated acylsilanes 5-13 in good to excellent yield.
https://doi.org/10.1021/jo00273a007
Synthesis and Structural Features of [4,4'-Diisopropoxyester-2,2'-bipyridine], [Dichloro(4,4'-diisopropoxyester-2,2'-bi-pyridine)-platinum(ii)] and Its Dichloromethane Solvated Pseudo-Polymorph: Versatile Supramolecular Interactions

Journal Article Browning, Charles; Nesterov, Vladimir; Wang, Xiaoping; ... - Journal of Chemical Crystallography

We report that the organic ligand 4,4'-diisopropoxyester-2,2'-bipyridine, C₁₈H₂₀N₂O₄ (1), crystallizes in the triclinic crystal system P-1 and the molecule occupies a special position in the unit cell. In the crystal, molecules form stacks with partial overlapping of the pyridine rings. The Pt(II) dichloro complex of 1 crystallizes from a mixture of ethanol/hexane and from dichloromethane to form orange and yellow crystals, respectively. The orange non-solvated crystals of the (bipyridine)(dichloro)platinum(II) complex C₁₈H₂₀N₂O₄PtCl₂ (2) crystallize in the triclinic crystal system P-1 as well with two independent molecules in the unit cell. In the crystal packing, molecules form two types of dimers withmore »« less
Cited by 6
https://doi.org/10.1007/s10870-015-0585-z

Full Text Available
1- and 2-(trialkylsilyl)ethanols: New silyl reagents from tin, lithium, and boron chemistry

Journal Article Soderquist, J; Rivera, I; Negron, A - Journal of Organic Chemistry; (USA)

Efficient preparations of isomerically pure 1- and 2-(trialkylsilyl)ethanols from vinylsilanes with borane reagents are described. In the former case, the borane reduction of the appropriate acetylsilane (12) gave good yields (82-94%) of the desired 1-R{sub 3}Si products (13, R = Me, Et, i-Pr). The reaction of ({alpha}-methoxyvinyl)lithium (10) (from Sn/Li exchange) with the appropriate chlorosilanes provided the corresponding ({alpha}-methoxyvinyl)silanes (11) (89-94%). Hydrolysis of 11 afforded acylsilanes (12) in excellent yield (93%). Hydroboration of the vinylsilanes (1) with 9-borabicyclo(3.3.1)nonane (9-BBN) gave ({beta}-borylethyl)silanes (2), which were oxidized to provide isomerically pure 2-silylethanols (3). The formation of Normant's reagent (4, vinylmagnesium bromide inmore »« less
https://doi.org/10.1021/jo00278a014
Primary deuterium isotope effects in the oxidation of Benzyl-a-d alcohol by transition elements and related reagents: mechanisms of electron transfer

Journal Article Kwart, H; George, T - J. Org. Chem.; (United States)

In order to assess the structural features of the activated complex in hydrogen transfer processes, benzyl-..cap alpha..-d alcohol has been oxidized to the aldehyde over a broad range of accurately controlled temperatures with four reagents: mangansese dioxide, nickel dioxide, cerium(IV), and 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ). Estimation of the benzaldehyde (C/sub 6/H/sub 5/CHO/C/sub 6/H/sub 5/CDO) product ratios was carried out by means of a mass spectrometric technique developed for the high precision measurements required in applying the data as a mechanistic criterion. The principal results are the striking temperature-dependent k/sub H/k/sub D/ values measured for the MnO/sub 2/ and NiO/sub 2/more »« less
https://doi.org/10.1021/jo01315a044

Similar Records