The polymerization of six spiro compounds such as
1-oxaspiro[2.5]octa-4,7-dien-6-one
(OSODO), spiro[anthrone-10,2‘-oxirane]
(SAO), and 5,7-dibromo-
(Br
2
-OSODO),
5,7-di-tert-butyl-
(tBu
2
-OSODO), 5,7-difluoro-
(F
2
-OSODO), and
4,5,7,8-tetrachloro-1-oxaspiro[2.5]octa-4,7-dien-6-ones
(Cl
4
-OSODO) were examined. Spiro compounds which carry substituents
at the 4 and 8 positions or bulky
substituents at the 5 and 7 positions such as SAO,
tBu
2
-OSODO, and
Cl
4
-OSODO were reluctant
to
undergo polymerization.
Br
2
-OSODO gave a
polymeric material in very low yield. OSODO and
F
2
-OSODO polymerized to give poly(1,4-phenylene oxide) and
poly(2,6-difluoro-1,4-phenylene oxide),
respectively. The polymerizability of these spiro compounds was
explained by the steric effect of the
substituents.
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