SCHEDULED MAINTENANCE
Synthesis and reactions of 3,3′-dibromodihydrodipyrrins
Abstract
The dibromodihydrodipyrrin diester 7 was prepared by reaction of
the corresponding pyrrole 6 with dimethoxymethane and
BF3·Et2O. Subsequently 7 was converted into
the dibromodihydrodipyrrin 2 in moderate yield. The
diformyldihydrodipyrrin 3 was readily prepared by methylenation of the
pyrrole 9 with BF3·Et2O, followed by
deprotection. Attempted synthesis of the porphyrin 1 from 2 and 3 was
unsuccessful because of the low reactivity of 2. The reaction of 7 or 11
with hexabutylditin in the presence of a Pd catalyst produced a new type
of tin complex 12 in low yield. This complex was also readily obtained
by an alternative procedure and found to revert to 7 upon reaction with
TFA.
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