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Structure and Reactivity of Xanthocorrinoids. Part III . The first example of a pinacol‐type rearrangement in the corrin series
Author(s) -
Grüning Burghard,
Holze Gerhard,
Gossauer Albert,
Ernst Ludger
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680632
Subject(s) - chemistry , corrin , vicinal , stereochemistry , reactivity (psychology) , acetic acid , carbonyl group , medicinal chemistry , group (periodic table) , pinacol , ascorbic acid , organic chemistry , ring (chemistry) , catalysis , medicine , alternative medicine , food science , pathology
The transformation of the c ‐acetic‐acid chain of hexamethyl Co α, Co β‐dicyanocobyrinate into an ethyl group (→ 2 ) as well as the synthesis of the pentadecaalkyl‐cobalticorrin 6d from commercial cyanocobalamin are described. On reaction of 2 or 6d with O 2 in the presence of ascorbic acid, migration of the CH 3 group at C(5) to the vicinal position C(6) takes place concomitantly with the introduction of a carbonyl group at C(5).