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5.2
Transition Metal Alkylidenes [28]
5.2.1
Group IVA and VA Transition Metal-Based Initiators
Though this topic focuses on late transition metals, the few well-defined Group
IVA- or VA-based systems that exist shall be outlined briefly. Among the first tran-
sition metal alkylidenes that were observed in ROMP was the bimetallic com-
pound (Cp 2 TiCH 2 ClAlMe 2 ) [29, 30]. Upon reaction with norborn-2-ene (bicyclo[2.2.1]
hept-2-ene, NBE) at ambient
temperature it forms the metallacycle shown in
Fig. 5.1 which opens at 65
C under ring-opening [31].
This system was the first well-documented example of a truly “living” [32-36]
ROMP. In analogy, Cp 2 TiMe 2 ,Cp 2 TiMe 3 ,Cp 2 TiMe 2 Cl, and Cp 2 Ti(CH 2 SiMe 3 ) 2 cat-
alyze the ROMP of NBE. The rate-determining step was proposed to be the loss
of CH 4 , ClCH 3 , and SiMe 4 , respectively [37]. Other Ti-alkylidenes exist, yet are not
of any significance to polymer chemistry [38].
Nb and Ta form a number of well defined and stable metal carbenes such as
Cl 2 CpTa(=CHCMe 3 ) and Cl 2 CpTa(=CHCMe 3 )PMe 3 [6, 39, 40]. In particular
Ta(=CHCMe 3 )(O-2,6-i-Pr 2 -C 6 H 3 ) 3 (THF) and Ta(=CHCMe 3 )(TIPT) 3 (TIPT=2,4,6-i-
Pr 3 -C 6 H 2 -S-) are good initiators for living ROMP [41, 42]. Ta[CMeCMeCHCMe 3 ]
(DIPP) 3 (DIPP=2,6-i-Pr 2 -C 6 H 4 -O), Fig. 5.2) has been reported to allow the living
polymerization of 2-butyne up to a degree of polymerization (DP) of 200 [43]. So
Fig. 5.1 Reaction of NBE with Cp 2 TiCH 2 ClAl(CH 3 ) 2 .
Fig. 5.2 Structure of Ta[CMeCMeCHCMe 3 ](DIPP) 3
(Ar =2,6-i-Pr 2 -C 6 H 3 ).
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