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Substituent‐Controlled Reactions of Iminophosphoranes with Methyllithium
Author(s) -
Steiner Alexander,
Stalke Dietmar
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199517521
Subject(s) - methyllithium , deprotonation , chemistry , substituent , reactivity (psychology) , medicinal chemistry , dimer , ring (chemistry) , monomer , amide , phosphorus , organic chemistry , medicine , ion , alternative medicine , pathology , polymer
Totally different reactivity is observed in the reactions of the two isoelectronic iminophosphoranes Py 3 P NSiMe 3 (Py = 2‐pyridyl) and Ph 3 P NSiMe 3 with methyllithium. While the first, even at −78 °C, spontaneously yields a monomeric amide on reduction of phosphorus( V ) to phosphorus( III ), the triphenyliminophosphorane yields the dimer 1 only after several days at room temperature in a deprotonation reaction of one phenyl ring in the ortho position.