Reactions of Organic and Organometallic Compounds with Solutions of Metals in Liquid Ammonia.

Watt, George W.

doi:10.1021/cr60144a003

Cited by 56 publications

(16 citation statements)

References 142 publications

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“…72,73,74 The regioselectivity of the Birch reduction depends on whether the substituent is electro-withdrawing or electro-donating. The intermediate radical anion tends to locate itself on the carbon ortho to an electro-withdrawing group and on the carbon meta to the electro-donating group in order to minimise the interactions.…”

Section: Aromatic Compoundsmentioning

confidence: 99%

The kinetics and mechanisms of organic reactions in liquid ammonia

Atherton

Page

2010

Faraday Discuss.

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Section: Aromatic Compoundsmentioning

confidence: 99%

The kinetics and mechanisms of organic reactions in liquid ammonia

Atherton

Page

2010

Faraday Discuss.

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“…While the hydroxyl group of ephedrine is preferentially reduced by an alkali metal in the presence of a proton source, such as water absorbed from the atmosphere, an excess of the alkali metal under these reaction conditions can lead to a further partial reduction of the aromatic ring of methamphetamine ( Fig. 1) (6)(7)(8)12,13). Because this ring reduced byproduct is not formed by other illicit manufacturing methods it serves as a marker of this method of manufacture in forensic casework.…”

mentioning

confidence: 99%

Structural Determination of the Principal Byproduct of the Lithium-Ammonia Reduction Method of Methamphetamine Manufacture

Person¹,

Meyer

Vyvyan

2005

Journal of Forensic Sciences

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One common method of illicit methamphetamine manufacture utilizes an alkali metal, typically lithium, and liquid ammonia to chemically reduce ephedrine or pseudoephedrine to form methamphetamine. This method is often referred to as the lithium-ammonia reduction method or the Birch reduction method. While the hydroxyl group of ephedrine is more reactive than the aromatic ring, excess alkali metal and the presence of a proton source allow the formation of a cyclohexadiene byproduct not found in samples of methamphetamine produced from other manufacturing methods. A sample enriched in this byproduct was generated and characterized using nuclear magnetic resonance (NMR) spectroscopy, gas chromatography-mass spectrometry (GC-MS), infrared (IR) spectrophotometry, and ultraviolet (UV) spectrophotometry. The chemical structure of this byproduct was determined to be 1-(1 ,4-cyclohexadienyl)-2-methylaminopropane (CMP).

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“…Several review articles have appeared that address the broad application of the chemistry (Watt, 1950;Birch, 1950;Birch, 1958). Organic phosphorous and sulfur compounds such as pesticides and chemical warfare agents are known to be reactive to solvated electrons (Kennedy et al, 1972).…”

Section: Background On the Chemistrymentioning

confidence: 99%

Application of the SOLV^TM Process: A Total Systems Approach to Environmental Remediation

Getman¹

1998

Remediation Journal

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He joined Commodore in Januury 1996, and is responsible for recommending and leading researcb in Commodore's Solvated Electron process, emerging tecbnologies, and business development. Key accomplisbments include expansion of tbe tecbnology for tbe destruction of dioxins, PAHs, explosives, and cbemical warfare agents. Dr. Getman obtained bis Ph.D. in organic cbembtryporn Rensselaer Polytecbnic Institute, Troy, New York in 1975.Commodore Solution Technologies, Inc. has developed an innovative total systems approach to environmental remediation that utilizes a patented chemistry called Solvated Electron Technology (SET"). Solvated electron solutions amsome of the mostpowe?ful reducing agents known. Formed by dhsolving alkali and alkaline-earth metals in anhydrous liquid ammonia to produce a solution of metal cations and free electrons, solvated electron solutions are capable ofproviding reductants ofgreat activity and uniqueness. Theyprovide a highly useful mechanism for the reductive destruction of many organic moleculesandareextremelyeflective in thedehalogenation of halogenated organic compounds. Commodore has received a nationwide EPA operating permit for the nonthemal destruction of PCBs using this process. The SoLFprocess is a total solution approach that incorporates S E P withpre-andpost-treatments, when necessary, forenvironmental cleanup. It is applicable to a broad range of substrates including liquids, solids, soils, and job materials. Z3is article presents results from several pilot, field, and commercial validation studies utilizing the SOL Fprocess.Functional organic compounds have proven to be some of the most difficult and expensive remediation challenges faced by the environmental cleanup industry. As a class, they represent some of the most toxic, environmentally persistent, and difficult-to-destroy compounds known. In the environment, materials such as pesticides, PCBs, dioxins, hrans, PAHs, BTXs, explosives, chemical warfare agents, chlorofluorocarbons, and chlorinated solvents are deemed to pose a hazard to health and the environment, even when present in relatively small quantities. To meet today's stringent cleanup standards, vast quantities of materials such as soil, job equipment, adsorbents, process liquids, and building materials must be treated to remove contaminants that may be present in quantities measurable only in parts-per-million.Other than landfill, commercially available remediation technology options principally are limited to thermal processes such as incineration, plasma arc, catalytic extraction, gas phase chemical reduction, and thermal desorption. These are undesirable due to generation of off gases such as

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Reactions of Organic and Organometallic Compounds with Solutions of Metals in Liquid Ammonia.

Cited by 56 publications

References 142 publications

The kinetics and mechanisms of organic reactions in liquid ammonia

The kinetics and mechanisms of organic reactions in liquid ammonia

Structural Determination of the Principal Byproduct of the Lithium-Ammonia Reduction Method of Methamphetamine Manufacture

Application of the SOLV^TM Process: A Total Systems Approach to Environmental Remediation

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Reactions of Organic and Organometallic Compounds with Solutions of Metals in Liquid Ammonia.

Cited by 56 publications

References 142 publications

The kinetics and mechanisms of organic reactions in liquid ammonia

The kinetics and mechanisms of organic reactions in liquid ammonia

Structural Determination of the Principal Byproduct of the Lithium-Ammonia Reduction Method of Methamphetamine Manufacture

Application of the SOLVTM Process: A Total Systems Approach to Environmental Remediation

Contact Info

Product

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Application of the SOLV^TM Process: A Total Systems Approach to Environmental Remediation