Publisher: Chemical Society of Nigeria

Synthesis of 1-(2-IODOETHYL)Pyrolidine-Substituted Cyclopentadiene and Their Transition Metal Complexes

G. U. Obuzor, B. L. Booth
KEYWORDS: THF = tetrahydrofuran, NaCp =cyclopentadiene).

ABSTRACT:

The  reaction  of  1-(2-iodoethyl)pyrrolidine  and  sodium  cyclopentadiene  (I:  1.5  ratio)  in tetrahydrofuran  (THF)  at  25  OC  under  argon  for  24hr,  afforded  after  hydrolysis  a  mixture  of  1-(2cyclopentadienylethyl)pyrrolidine.  The  mixture  was  purified  by  fractional  distillation  under  reduced pressure  to  give  the  desired  product  as  a  mixture  of  two  isomers,  b.p.  (98I04  OC/lmm  Hg)  in  79% yield.  The  isomers  were  characterized  by  '13C,  1H  NMR  (300MHZ,  D2O)  IR,  Microanalysis  and  Mass Spec.    The  complexation  of  the  combustible  lithium  salt  of  1-(2-cyclopentadienylethyl)pyrrolidine  and Zirconium  tetrachloride  (ZrCI4)  under  argon  in  air-free  anhydrous  dimethoxyethane  at  80  OC  to room temperature  for  three  days  gave  the  desired  product  after  work-up  as  a  viscous  red  oil  MS(FAB)m/z 322  (C  IIHI7NZrCI2)73%.  The  oil  was  stable  under  argon.  The  titanium  complex  MS(FAB)m/z 277(CIIH17NTiCI4)  was  obtained  by  the  reaction  of  the  lithium  salt  of  I-(2cyclopentadienylethyl)pyrrolidine  with  TiCI4.2THF  in  THF  as  a  green  mixture  and  is  stable  only  in THF.  


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