101055-70-3

Basic information

• Product Name: 1-ADAMANTYLPHOSPHAETHYNE
• Synonyms: Phosphine,(tricyclo[3.3.1.13,7]dec-1-ylmethylidyne)-
• CAS NO: 101055-70-3
• Molecular Formula: C₁₁H₁₅P
• Molecular Weight: 178.21
• Mol File: 101055-70-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 69 °C
• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: 1-ADAMANTYLPHOSPHAETHYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ADAMANTYLPHOSPHAETHYNE(101055-70-3)
• EPA Substance Registry System: 1-ADAMANTYLPHOSPHAETHYNE(101055-70-3)

Safety Data

• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 101055-70-3(Hazardous Substances Data)

Usage

Composition

Phosphorus atom bonded to an ethynyl group and an adamantyl group

Type of bond

Stable phosphorus-carbon triple bond

Field of study

Organophosphorus chemistry

Stability

High stability

Thermal resistance

High thermal resistance

Applications

Development of new materials, building block for synthesis of complex organic molecules

Interest

Exploration as a ligand in coordination chemistry, design of novel molecular systems for various technological applications

Unique structure

Sparked interest in its potential applications and reactivity

InChI:InChI=1/C11H15P/c12-7-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10H,1-6H2

Upstream product

• 105395-83-3 1-Adamantoyl-bisphosphine 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 105395-80-0 (E)-(Adamant-1-yl-trimethylsiloxy)-methylidene-trimethylsilylphosphine 

Downstream Products

• 765279-28-5 (C₅H₅)2Ti(C(C₁₀H₁₅)P(CC₆H₅)2) 
• 118398-75-7 2-(Adamant-1-yl)-1-chlor-3-phenyl-1H-phosphiren 
• 74203-39-7 (3r,5r,7r)-1-(phenylethynyl)adamantane 
• 105395-82-2 5-(Adamant-1-yl)-3-benzoyl-1H-1,2,4-diazaphosphole 

Relevant articles and documents

Phosphaalkynes from acid chlorides via P for O(CI) metathesis: A recyclable niobium phosphide (P3-) reagent that effects C-P triple-bond formation

Reported herein is a new, metathetical P for O(Cl) exchange mediated by an anionic niobium phosphide complex that furnished phosphaalkynes (RC≡P) from acid chlorides (RC(O)Cl) under mild conditions. The niobaziridine hydride complex, Nb(H)(tBu(H)C=NAr)(N[Np]Ar)2 (1, Np = neopentyl, Ar = 3,5-Me2C6H3), has been shown previously to react with elemental phosphorus (P4), affording the μ-diphosphide complex, (μ2:η2,η2-P2)[Nb(N[Np]Ar)3]2, (2), which can be subsequently reduced by sodium amalgam to the anonic, terminal phosphide complex, [Na][PNb(N[Np]Ar)3] (3). It is now shown that treatment of 3 with either pivaloyl (t-BuC(O)Cl) or 1-adamantoyl (1-AdC(O)Cl) chloride provides the thermally unstable niobacyles, (t-BuC(O)P)Nb(N[Np]Ar)3 (4-t-Bu) and (1-AdC(O)P)Nb(N[Np]Ar)3 (4-1-Ad), which are intermediates along the pathway to ejection of the known phosphaalkynes t-BuC≡P (5-t-Bu) and 1-AdC≡P(5-1-Ad). Phosphaalkyne ejection from 4-t-Bu and 4-1-Ad proceeds with formation of the niobium(V) oxo complex ONb(N[Np]Ar)3 (6) as a stable byproduct. Preliminary kinetic measurements for fragmentation of 4-t-Bu to 5-t-Bu and 6 in C6D6 solution are consistent with a first-order process, yielding the thermodynamic parameters ΔH? = 24.9 ± 1.4 kcal mol-1 and ΔS? = 2.4 ± 4.3 cal mol-1 K-1 over the temperature range 308-338 K. Separation of volatile 5-t-Bu from 6 after thermolysis has been readily achieved by vacuum transfer in yields of 90%. Pure 6 is recovered after vacuum transfer and can be treated with 1.0 equiv of triflic anhydride (Tf2O, Tf = O2SCF3) to afford the bistriflate complex, Nb(OTf)2(N[Np]Ar)3 (7), in high yield. Complex 7 provides direct access to 1 upon reduction with magnesium anthracene, thus completing a cycle of element activation, small-molecule generation via metathetical P-atom transfer, and deoxygenative recycling of the final niobium(V) oxo product. Copyright