Lithium naphthalenide

Base Information

• Chemical Name: Lithium naphthalenide
• CAS No.: 14474-59-0
• Molecular Formula: C10H7Li
• Molecular Weight: 134.107
• DSSTox Substance ID: DTXSID70472033
• Mol file: 14474-59-0.mol

Synonyms:lithium naphthalenide;1-naphthyl lithium;14474-59-0;DTXSID70472033;GQNMAZUQZDEAFI-UHFFFAOYSA-N;ZATOFRITFRPYBT-UHFFFAOYSA-N

Chemical Property of Lithium naphthalenide

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 134.07077866
• Heavy Atom Count: 11
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [Li+].C1=CC=C2[C-]=CC=CC2=C1

Technology Process of Lithium naphthalenide

There total 1 articles about Lithium naphthalenide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

diethyl ether (60-29-7,927820-24-4) + 1-Bromonaphthalene (90-11-9) → PERYLENE (198-55-0) + naphthalen-1-yl-lithium (14474-59-0)

Guidance literature:

DOI:10.1080/03946975.2002.10531171 DOI:10.1021/ja01170a076

Reference yield: 72.0%

naphthalen-1-yl-lithium (14474-59-0) → 1-Fluoronaphthalene (321-38-0)

Guidance literature:

With sultam (C₆H₄C₃H₆NFSO₂); In tetrahydrofuran; at -75 ℃; Rate constant; k_obs/kET;

DOI:10.1016/S0040-4039(00)79384-1

Reference yield: 63.0%

naphthalen-1-yl-lithium (14474-59-0) → α-naphthol (90-15-3)

Guidance literature:

With 2-t-butylperoxy-1,3,2-dioxaborolane; In tetrahydrofuran; 1.) overnight, 2.) reflux, 3 h;

DOI:10.1055/s-1983-30236

upstream raw materials:

diethyl ether

1-Bromonaphthalene

Downstream raw materials:

2-naphthylpyridine

naphthalen-1-yl(phenyl)(pyridin-2-yl)methanol

1-naphthyl phosphonic acid

rac-(-)-(1R,2S)-2-(naphthalen-1-yl)cyclohexan-1-ol

Refernces

Oxazolidinone-promoted, torquoselective Nazarov cyclizations

10.1021/ol300316a

The research explores the use of oxazolidinones as promoters in the Nazarov cyclization reaction, enabling the cyclization of typically resistant substrates under mild conditions. The study highlights the excellent regio- and torquoselective control exerted by oxazolidinones in both conventional and "interrupted" Nazarov reactions, leading to the formation of cyclopentanoid structures such as cyclopentenones and indenones. Key chemicals involved in the research include oxazolidinone-substituted Nazarov substrates synthesized from ynamides through various palladium-mediated coupling techniques, such as reductive coupling with acid chlorides and carbonylative couplings. The cyclization reactions were facilitated by methanesulfonic acid (MeSO3H) or triflic acid (TfOH) in nonpolar solvents like dichloromethane or toluene. The oxazolidinone auxiliary was later cleaved using lithium naphthalenide (LiNp) or SmI2, yielding the desired products with good yield and enantiomeric excess.