61417-19-4

Usage

Uses

Used in Fuel Technology:
1,1'-Ethynylenebisadamantane is used as a high-energy fuel additive for its potential to enhance the energy density and performance of fuels.
Used in Materials Science:
1,1'-Ethynylenebisadamantane is used as a polymer additive for its ability to improve thermal stability and flame resistance, making it suitable for applications requiring high-temperature resistance or flame retardancy.
Used in Pharmacology:
1,1'-Ethynylenebisadamantane is studied as a potential pharmacological agent due to its unique molecular structure and potential for biological activity, indicating its possible use in the development of new drugs or therapeutic agents.

Upstream product

• 762-42-5 dimethyl acetylenedicarboxylate 
• 317363-70-5 2,3-di-(1-adamantyl)thiirene 1-oxide 
• 209208-05-9 4,5-di(1-adamantyl)-1,2,3-trithiole 2-oxide 
• 75-15-0 carbon disulfide 
• 54251-54-6 Adamantyldiazomethan 
• 768-90-1 1-Adamantyl bromide 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 101055-70-3 1-adamantylphosphaacetylene 

Relevant academic research and scientific papers

Synthesis and characterization of aliphatic α-dithiones, di(1-adamantyl)- and di-tert-butylethanedithiones

2,3-Di(1-adamantyl)thiirene 1-oxide quickly reacted with Lawesson's reagent in CH2Cl2 at room temperature to provide di(1-adamantyl)ethanedithione (1) as thermally labile, violet crystals in 20% isolated yield. The use of CS2 as the solvent gave 1 in 46% isolated yield. The reaction in the presence of dimethyl acetylenedicarboxylate furnished dimethyl 4,5-di(1-adamantyl)-2,3-thiophenedicarboxylate in 51% yield. A tentative mechanism for the formation of 1 is proposed on the basis of the experimental observations. The structure of 1 was characterized on the basis of spectroscopic data (NMR, mass, IR, Raman, and UV/vis) and DFT calculations. 1 rearranged to 3,4-di(1-adamantyl)-1,2-dithiete quantitatively with kinetic parameters of ΔH? = 17.6 ± 0.2 kcal mol-1, ΔS? = -23.0 ± 0.7 cal K-1 mol-1, and ΔG? = 24.4 ± 0.4 kcal mol-1. Peracid oxidation and Pt-complex formation of 1 are also reported. Copyright

Organophosphorus compounds, part 146 imidovanadium(V) complexes as reaction partners for kinetically stabilized phosphaalkynes. Synthesis and reactivity of 3-Aza-1,2,4,6-tetraphospha-quadricyclanes

The Lewis base adducts of imidovanadium(V) compounds 5a,b undergo chemoselective cyclooligomerization reactions with the kinetically stabilized phosphaalkynes 4a-e to furnish the azatetraphosphaquadricyclanes 6a-f with incorporation of the imido fragment. The reactivity of this novel class of heteropolycyclic compounds has been examined exemplarily for compound 6a. Complexation of one and two phosphorus atoms was achieved by reaction with nonacarbonyldiiron or the tungsten pentacarbonyl-THF complex resulting in the formation of the transition metal compounds 17-20. Reactions of 6a with the sulfonyl azides 21a-c furnished the Staudinger products 22a-c. The reaction of 6a with two equivalents of tosyl azide gave a surprising result. No double complexation leading to a symmetrical product was achieved, and compound 23 was obtained instead in which the two phosphorus atoms of one diphosphirane ring are functionalized. Oxidative cleavage of a P/P bond in 6a to furnish product 24 is observed in the reaction of 6a with the Lewis base-free imidovanadium(V) species 15a.

Ring-Opening and Ring-Expansion Study of 3,4-Di(1-adamantyl)-1,2-dithiete

Reduction of 3,4-di(1-adamantyl)-1,2-dithiete (2) with LiEt3BH, followed by treatment with Mel, gave (E)-1,2-di(1-adamantyl)-1,2-bis(methylthio)ethene (7-E) in 87% yield. Configuration of the double bond part of 7-E was determined by X-ray diff

m-Chloroperbenzoic acid oxidation of 1,2-dithietes: First synthesis and characterization of 1,2-dithiete S-oxides and ethane-1,2-dithione S,S'-dioxides (α-disulfines)

Oxidation of 1,2-dithietes with 1 equiv of MCPBA gives the corresponding 1,2-dithiete S-oxides, while oxidation with more than 2 equiv of MCPBA affords three geometrical isomers of ethane-1,2-dithione S,S'-dioxides (α-disulfines) with opening of the four-

Small Rings, 90. - Peralkyl-Substituted Tetrahedranes

Photolysis of the diazo compounds 4a, b generates adamantyltri-tert-butyltetrahedrane (9a) and tri-tert-butylisopropyltetrahedrane (9b), and the corresponding cyclobutadienes 10a, b.In contrast to tetrahedrane 9a, which results from an intramolecular addition in carbene 7a and also from photoisomerization of cyclobutadiene 10a, the only source for tetrahedrane 9b is the cheletropic cycloaddition of the carbenic center to the cyclopropene double bond in the photochemically produced carbene 7b.Tetrahedrane 9b is remarkable in its kinetic and thermal instability, which is caused by the reduced "corset effect" in this compoound.An additional access to this tetrahedrane is possible via the diazomethanes 34A and 34B.The pyridazines 17b and 41, which are formed by thermolysis of the diazo compounds 4b, 34A and 34B lead to the azetes 19 and 43.Last but not least 17b and 41 are interesting molecules themselves because of their inherent chirality. - Key Words: Tetrahedranes / Cyclobutadienes / Azetes / Cyclopropenyldiazomethanes / Pyridazines: chirality, ring inversion, valence isomers

The Electron Spin Resonance Spectra of 1-Adamantanylcyclobutadiene Radical Cations

By photolysing solutions of the appropriate alkynes and aluminium chloride in dichloromethane, the following cyclobutadiene radical cations have been generated, and their e.s.r. spectra recorded: 1-Ad4C4+., (-1-Ad)4C4+., (-1-Ad)4C4+., cis- and trans-Me2-1-Ad2C4+., and cis-Et2-1-Ad2C4+. (1-Ad=1-adamantanyl).It is concluded that in 1-Ad4C4+., the bulky adamantanyl groups cause the central ring to distort from planar, but that there is no restriction of rotation about the adamantanyl-ring bond, and that proton hyperfine coupling to the δ-CH group is larger than to the γ-CH2 groups.In the e.s.r. spectra of the deuteriated compounds, a variety of 13C satellites can be distinguished, and they have been assigned using probability theory.The interpretation of the spectra is supported by UMINDO/3-INDO calculations.In cis-Me2-1-Ad2C4+., a (Me) is lower, and in trans-Me2-1-Ad2C4+. it is higher, than in Me4C4+..The various steric and electronic effects, and solvent and counterion interactions, which may contribute to this ordering, are discussed.

SYNTHESIS OF TERTIARY ALKYL-SUBSTITUTED ACETYLENES BY ELECTROPHILIC ADDITION TO SILYLACETYLENES

The reaction of silylacetylenes 6-8 with tertiary alkyl halides 11-13 under Lewis acid catalysis affords tertiary alkyl-substituted acetylenes 1-5.The reaction occurs under mild conditions (from -78 to -17 deg C) and requires fairly short times (1-6 h).Se

One-step Synthesis of Tertiary Alkyl-substituted Acetylenes from Silylacetylenes

The reaction of silylacetylenes with tertiary alkyl halides under Lewis acid catalysis gives tertiary alkyl-substituted alkynes in high yields.