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Migratory aptitudes in pinacol rearrangement of vic ‐dihydroxychlorins
Author(s) -
Chang C. K.,
Sotiriou Chariklia
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220654
Subject(s) - chemistry , side chain , pinacol , alkyl , propionate , cope rearrangement , medicinal chemistry , carroll rearrangement , stereochemistry , organic chemistry , sigmatropic reaction , catalysis , polymer
When vic ‐dihydroxychlorins undergo a pinacol‐pinacolone rearrangement, the migratory aptitudes of common porphyrin substituents follow the order: alkyl groups, propionate side chain, H > methyl group > acetate side chain. C ‐Alkylchlorins can be made by extremely short syntheses utilizing such rearrangement.