82537-28-8

Basic information

• Product Name: Lithium, [(triphenylphosphoranylidene)methyl]-
• CAS NO: 82537-28-8
• Molecular Formula: C19H16LiP
• Molecular Weight: 282.251
• Mol File: 82537-28-8.mol

Chemical Properties

• CAS DataBase Reference: Lithium, [(triphenylphosphoranylidene)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Lithium, [(triphenylphosphoranylidene)methyl]-(82537-28-8)
• EPA Substance Registry System: Lithium, [(triphenylphosphoranylidene)methyl]-(82537-28-8)

Safety Data

• Hazardous Substances Data: 82537-28-8(Hazardous Substances Data)

Upstream product

• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 917-54-4 methyllithium 
• 19493-09-5 Methylenetriphenylphosphorane 
• 594-19-4 tert.-butyl lithium 
• 598-30-1 sec.-butyllithium 
• 29949-93-7 iodomethylenetriphenylphosphorane 
• 591-51-5 phenyllithium 

Downstream Products

• 600738-46-3 phenyl{bis(triphenylphosphanemethylenido)}borane 
• 91986-27-5 (C₅H₅)2Lu(C₆H₄)CH₂P(C₆H₅)2 
• 788792-90-5 [(R)-4-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-triphenyl-phosphonium 
• 95881-13-3 (6Z,9Z,11Z)-8-Methylene-5,13-diphenyl-8H-cyclonona[b]naphthalene 

Relevant articles and documents

Interaction of t-butyllithium and triphenylmethylenephosphoranes

NMR experiments show that a directed ortho-metalation occurs at one of the aromatic rings of triphenylmethylenephosphoranes (Ph3P-CHR, R = H, Me) when the phosphorus ylide is treated with 1 equiv. t-BuLi. If pre- coordination of t-BuLi is inhibited by a sterically demanding and electron- withdrawing substituent (R = SiMe3) no metalation is observed. (C) 2000 Elsevier Science Ltd.

An Efficient Synthesis of (22E,25R)-1α,25,26-Trihydroxy-Δ22-Vitamin D3

The title compound 2 was prepared from C22-aldehyde 3 in 51 percent overall yield.The key feature of this synthesis is a one-pot construction of the requisite side chain using α-lithiomethylenetriphenylphosphorane 4 and commercially available (S)-2-methylglycidol.

NEW EVIDENCE FOR AND NEW REACTIONS OF ORTHO-LITHIO YLIDS

While α-lithio ylid 2 may be generated from triphenylphosphonio-bromomethylid through halogen/metal exchange, the reaction of triphenylphosphonio-methylid 1 with sec- or tert-butyllithium produces nearly quantitatively the o-lithio ylid 3, which is stable at -60 deg C but slowly decomposes at higher temperatures via a cyclization product 5 to give the α-lithio phosphine 4.

ORTHO-LITHIATION OF TRIPHENYLPHOSPHINO-METHYLID AND, ALSO, TRIPHENYLPHOSPHINE OXIDE

While upon treatment with methyl- or butyllithium triphenylphosphonio-methylid (1) undergoes extensive ligand exchange (leading to 4) it reacts with sec- or tert-butyllithium mainly at the ortho-position exchanging one hydrogen against a lithium atom (to give 3).