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Petroleum Origin and Generation
Published in Muhammad Abdul Quddus, Petroleum Science and Technology, 2021
The letters (s, l, g) represent solid, liquid and gas states. Acetylene gas is a highly reactive substance, and rapidly undergoes various additive, substitution, oxidation and polymerization reactions, producing a variety of organic chemicals. Similarly other inorganic chemicals, carbon dioxide, water and alkali metals could be used to produce sodium acetylide (Na–C=CH). Acetylide is convertible to organic acetylene gas. Additionally, a number of hydrocarbon compounds are commonly synthesized from two inorganic gases, namely carbon monoxide and hydrogen, in the presence of a catalyst at suitable temperature and pressure. The same concept of organic synthesis could be applied in the natural generation and accumulation of hydrocarbons in the subsurface rock through the interaction of inorganic chemicals. Did such conditions exist in the deep earth crust for the formation and preservation of organic chemicals? Having said that, is this inorganic phenomenon enough to correlate with the large quantities with varying chemical and structural properties of organic matter found the world over? The answer is most probably no. Alternate theories are given below.
Applied Chemistry and Physics
Published in Robert A. Burke, Applied Chemistry and Physics, 2020
Silver acetylide (silver carbide), C2Ag2, is also an inorganic explosive that is highly sensitive and cannot be used in detonators. Silver acetylide is a primary explosive. It is a white powder that is sensitive to light. Generally, a chemical explosive must be confined for an explosion to take place. However, silver acetylide maintains a high-energy density and will detonate without confinement. Dry silver acetylide poses an explosion hazard when exposed to heat, shock or friction. When dry, it should not be stored indoors. Because it is light sensitive, it should be stored in a dark room. It should also be stored in an amber bottle.
Aldehydes and Ketones. Acyl Addition Reactions
Published in Michael B. Smith, A Q&A Approach to Organic Chemistry, 2020
Acetylide is formally the carbanion form of acetylene (ethyne) formed by removal of a hydrogen atom by base. The term acetylide is sometimes used generically for an alkyne anion R–C≡C:–. How are alkyne anions formed?
Silver iodide catalyzed the three-component reaction between terminal alkynes, carbon disulfide, and aziridines
Published in Journal of Sulfur Chemistry, 2019
Terminal alkynes are valuable synthons in the synthesis of a wide range of organic molecules [1–3]. Conversion of terminal alkynes to the corresponding acetylides take place either in the presence of a strong base or using an appropriate catalyst system. The latter method takes advantage of simplicity, compatibility with a wide range of functional groups and protic solvents. Particularly, the nucleophilic additions of metal-acetylides to Michael acceptors serve as an efficient method for the synthesis of highly desirable C–C bond from the readily accessible substrates [4–9]. In last decade, the development of catalytic formations of metal-acetylides offers an opportunity for the expedient synthesis of complex molecules from such simple starting materials [10–12]. In most of these transformations, copper salts were selected as the catalysts of choice based on the cost, tolerability with functional groups, and efficiency [13–16]. It is worth mentioning that the oxidation states of copper salts have tiny effect on metal-acetylides formation. For instance, Carreira and co-workers reported the first nucleophilic additions of copper-acetylides into unsaturated carbonyl in aqueous reaction medium using Cu(II)/ascorbate as catalyst system [17]. Particularly notable is the use of copper-acetylide as an organometallic species in such protic reaction medium. Additionally, their reports on nucleophilic additions of copper-acetylides to carbonyl and imine moieties were without precedent [18,19]. Recently, Garcia-Tellado reported an enantioselective route for the synthesis of chiral propargylic amines based on the nucleophilic addition of metal-acetylides into α-imino esters [20]. The pioneering work of Medal in use of copper-acetylides with azides has also attracted much attentions owing to its compatibility toward synthesis of a variety of functional groups and heterocycles [21–25]. To our knowledge, Ghazanfarpour reported the first addition of copper-acetylides to carbon disulfide, allowing efficient access to 1,4-oxathiane skeletons [26]. Our group have also disclosed a reaction involving terminal alkynes, isothiocyanates, and oxiranes using silver salts as a catalyst [27]. Our recent report on the reaction of copper-acetylides, isothiocyanates, and aziridines leads to the formation of thiomorpholine derivatives in good yields [28]. Based on the above literatures and in continuation of our reports in synthesis of heterocycles [29,30], we became interested to explore the efficiency of silver-acetylides in a catalytic multicomponent reaction that uses carbon disulfide and aziridines.