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1 group of the intermediate for 1 attacks at the α′-position (5-position) of the TEG-tethered pyrrole to give the corresponding porphyrinogen, whereas that for 2 substitutes the α-position (2-position) of the alkyl-tethered pyrrole. The difference in the reactivity between the α- and the α′-carbons of the β-mono-substituted pyrrole rings may cause the excessive yield of 2 over 1 under the condition.
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70350506743
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note
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+ promotes the scrambling reaction. Probably, because 1,2-dichloroethane contains a little amount of acid and it may cause a worse isomeric ratio 2/1 than EtOH.
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70350506742
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note
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A referee suggested the possibility that the precipitate of the short rod-like structure is crystallographically a chiral twin and that of the helical ribbon structure is chiral. At present, however, we have no evidence to support the possibility and thus we just mention the possibility here.
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