do not need to formally request permission to reproduce material contained in this
"Reproduced from" can be substituted with "Adapted from". D. H. Froemsdorf, H. R. Pinnick and S. Meyrson, Instructions for using Copyright Clearance Center page. Fisher DM, Canfell PC, Fahey MR, et al. it in a third party non-RSC publication you must Gas phase analogues of cage effects. Structural Effects on the gas phase reactivity of organic salt complexes: substitution versus Hofmann elimination. View or download all the content the society has access to. Create a link to share a read only version of this article with your colleagues and friends. You can be signed in via any or all of the methods shown below at the same time. Please read and accept the terms and conditions and check the box to generate a sharing link. Stereochemical analysis of deuterated alkyl chains by MS/MS. Gamini Gunawardena from the OChemPal site (Utah Valley University) Back to top; Hofmann … For more information view the SAGE Journals Sharing page. Stereochemistry of Hofmann elimination in a simple acyclic system . Some society journals require you to create a personal profile, then activate your society account, You are adding the following journals to your email alerts, Did you struggle to get access to this article? Gas phase analogues of cage effects. Hofmann elimination is a type of elimination reaction of an amine, where the least stable or least substituted alkene, called the Hofmann product, is formed. For the 3-hexyl series of threo and erythro 4-monodeuterated ions (3-hexylammonium ion; N,N,N-trimethyl-d3-3-hexylammonium ion; N-ethyl-3-hexylammonium ion; N-methyl, N-ethyl-3-hexylammonium ion; N,N-dimethyl, N-ethyl-3-hexylammonium ion), the upper limit of the E:Z ratio of the expelled alkene (r) approaches 2 (the stereospecificity) with a deuterium isotope effect close to 2.0, although the effects of isotopic substitution diminish the E:Z ratio somewhat.
Download Citation | Hofmann elimination | Elimination reaction of alkyl trimethyl amines proceeds with anti-stereochemistry, furnishing the least highly substituted olefins. The e-mail addresses that you supply to use this service will not be used for any other purpose without your consent. Fisher DM, Canfell PC, Fahey MR, et al. The first page of this article is displayed as the abstract. This product could help you, Accessing resources off campus can be a challenge.
It is named after its discoverer, August Wilhelm von Hofmann. Contact us if you experience any difficulty logging in. For example, trans-2-methyl-1-chlorocyclohexane reacts with alcoholic KOH at a much slower rate than does its cis-isomer.
Mechanism of elimination reactions. Hofmann elimination is an elimination reaction of an amine where the least stable (least substituted) alkene, the Hofmann product, is formed. For the 3-hexyl series of threo and erythro 4-monodeuterated ions (3-hexylammonium ion; N,N,N-trimethyl-d3-3-hexylammonium ion; N-ethyl-3-hexylammonium ion; N-methyl, N-ethyl-3-hexylammonium ion; N,N-dimethyl, N-ethyl-3-hexylammonium ion), the upper limit of the E:Z ratio of the expelled alkene (r) approaches 2 (the stereospecificity) with a deuterium isotope effect close to 2.0, although the effects of isotopic substitution diminish the E:Z ratio somewhat.
It is named after its discoverer, August Wilhelm von Hofmann. Avec des amines asymétriques, l'alcène majoritairement formé est le moins substitué et généralement le moins stable, une caractéristique appelée "Règle d'Hofmann". the whole article in a third party publication with the exception of reproduction Alston TA. La dernière modification de cette page a été faite le 7 novembre 2019 à 23:11. The email address and/or password entered does not match our records, please check and try again. C'est l'opposé de ce qui se passe avec une réaction d'élimination normale où le produit le plus stable est majoritaire.
or in a thesis or dissertation provided that the correct acknowledgement is given View or download all content the institution has subscribed to. Propose a structure for the intermediate, and explain why it readily undergoes elimination. Two fragmentations compete with that reaction: hydride shift (which gives the same products but with hydrogen scrambling) and loss of a neutral amine to give an alkyl cation. Morizur JP, Taphanel MH, Mayer PS, et al. article provided that the correct acknowledgement is given with the reproduced material. An explanation of the, The effect of ion pairing on the stereochemistry of elimination from quaternary ammonium salts, Collision-induced dissociation mass spectra of protonated alkylamines, Mechanistic study of the gas-phase in-source Hofmann elimination of doubly quaternized cinchona-alkaloid based phase-transfer catalysts by (+)-electrospray ionization/tandem mass spectrometry, How does acetylcholine lose trimethylamine? Après la première étape, un sel d'iodure d'ammonium quaternaire est créé. Please check you selected the correct society from the list and entered the user name and password you use to log in to your society website. Veith HJ. If you are the author of this article you still need to obtain permission to reproduce 23.33). with the reproduced material. Stereochemical analysis of monodeuterated isomers by GC/MS/MS. It is named after its discoverer, August Wilhelm von Hofmann.[1][2]. "Reproduced from" can be substituted with "Adapted from". XX is the XXth reference in the list of references. McAdoo DJ and Morton TH. Simply select your manager software from the list below and click on download. of the whole article in a thesis or dissertation.
of the whole article in a thesis or dissertation. Reproduced material should be attributed as follows: If the material has been adapted instead of reproduced from the original RSC publication
I have read and accept the terms and conditions, View permissions information for this article. Stereochemistry of Hofmann elimination in a simple acyclic system D. H. Froemsdorf, H. R. Pinnick and S. Meyrson, Chem. These competing reactions render our calculation approximate, but the results suggest a value not too far from the upper limit. L'élimination de Hofmann, aussi connue sous le nom de méthylation exhaustive, est une réaction où une amine réagit pour former une amine tertiaire et un alcène, par excès d'iodométhane, suivie par une réaction avec de l'oxyde d'argent, de l'eau, et apport de chaleur[1].
stereochemistry of the Hofmann elimination without having to consider interactions between the base and the quaternizedsalt, which rendersyn and anti-transition states comparable in energy.2,3 The absence of base in the gas phase also makes it possible to look at proto-nated amines in addition to quaternary ammonium ions. Please check you selected the correct society from the list and entered the user name and password you use to log in to your society website. McAdoo DJ and Morton TH. with the reproduced material. Veith HJ. View or download all content the institution has subscribed to. Instructions for using Copyright Clearance Center page for details. Some society journals require you to create a personal profile, then activate your society account, You are adding the following journals to your email alerts, Did you struggle to get access to this article? The first page of this article is displayed as the abstract. Collisonal activation of quaternary ammonium ions produced by field desorption.
The Hofmann elimination of ammonium ions having a single positive charge is demonstrated to exhibit stereospecificity with regard to expulsion of neutral alkene. https://fr.wikipedia.org/w/index.php?title=Élimination_de_Hofmann&oldid=164292860, licence Creative Commons attribution, partage dans les mêmes conditions, comment citer les auteurs et mentionner la licence. Hofmann Elimination Last updated Aug 24, 2020; Save as PDF Hofmann Degradation; Hofmann Rearrangement; Donate. Members of _ can log in with their society credentials below, Bruno Figadére, Tangyuan Cao, and Thomas H Morton. New login is not successful because the max limit of logins for this user account has been reached. Fetching data from CrossRef. is available on our Permission Requests page. 23.21, p. 1132), conversion of the ammonium salt to the hydroxide (Eq. In all cases the Ref. Access to society journal content varies across our titles.
D. H. Froemsdorf, H. R. Pinnick and S. Meyrson, Instructions for using Copyright Clearance Center page. If you are the author of this article you do not need to formally request permission and Seymour Meyrson Abstract. Fragment ion formation of quaternary ammonium salts under fast atom bombardment and field desorption collisionally activated dissociation conditions. Access to society journal content varies across our titles. Contact us if you experience any difficulty logging in. You do not have JavaScript enabled. Fetching data from CrossRef.
XX is the XXth reference in the list of references. Contributors and Attributions; Contributors and Attributions. The Hofmann elimination, known for more than a century and a half, can proceed by a variety of mechanisms. Saunders Jr., WH, Bailey DS, Montgomery FC, et al. This may take some time to load. Gronert S and Fong L-M. Collisonal activation of quaternary ammonium ions produced by field desorption.
In all cases the Ref. Go to our
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