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Reactivity of Iminophosphoranes. Formation of the Piperazine Ring
Author(s) -
Lin TuChen,
Cheng MingChu,
Peng Shie Ming,
Liu ShiuhTzung,
Kiang FuMei
Publication year - 1995
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199500071
Subject(s) - chemistry , piperazine , reactivity (psychology) , triphenylphosphine , intramolecular force , ring (chemistry) , medicinal chemistry , intermolecular force , lithium (medication) , hydrolysis , photochemistry , stereochemistry , organic chemistry , molecule , catalysis , medicine , alternative medicine , pathology , endocrinology
Reaction of 3‐azidopropyl methanesulfonate with triphenylphosphine produced the 1,4‐bis(triphenyl‐phosphino)piperazine 5 by intermolecular cyclization, instead of formation azidine derivatives by an intramolecular pathway. Structural formulation of 5 was achieved by both spectral and X‐ray crystal analysis. Hydrolysis of 5 under basic condition gives piperazine, whereas reaction of lithium diphenylphosphide with 5 produced 1,2‐bis(diphenyl‐phosphino)ethane (dppe) exclusively.