93746-77-1Relevant academic research and scientific papers
Interaction of t-butyllithium and triphenylmethylenephosphoranes
Korth, Karsten,Sundermeyer, J?rg
, p. 5461 - 5464 (2007/10/03)
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.
NEW EVIDENCE FOR AND NEW REACTIONS OF ORTHO-LITHIO YLIDS
Schaub, Bruno,Schlosser, Manfred
, p. 1623 - 1626 (2007/10/02)
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
Schaub, Bruno,Jenny, Titus,Schlosser, Manfred
, p. 4097 - 4100 (2007/10/02)
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).
