Cobryketone Derived from Vitamin B12 via Palladium-Catalyzed Cleavage of the sp3–sp3 Carbon–Carbon Bond

Heptamethyl cobyrinate was transformed into hexamethyl 8-nor-cobyrinate. The crucial step involved the synthesis of new, vitamin B12 derived cobryketone via palladium-catalyzed cleavage of the sp3–sp3 carbon–carbon bond with the liberation of the ketone. The replacement of sp3 carbon atom with sp2 (...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-04, Vol.78 (8), p.4115-4122
Main Authors: Kurcoń, Sylwester, Proinsias, Keith ó, Gryko, Dorota
Format: Article
Language:English
Subjects:
Catalysis
Electrons
Ketones - chemistry
Molecular Structure
Palladium - chemistry
Vitamin B 12 - chemistry
Online Access:Get full text
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Summary:Heptamethyl cobyrinate was transformed into hexamethyl 8-nor-cobyrinate. The crucial step involved the synthesis of new, vitamin B12 derived cobryketone via palladium-catalyzed cleavage of the sp3–sp3 carbon–carbon bond with the liberation of the ketone. The replacement of sp3 carbon atom with sp2 (CO) at the 8-position produces a bathochromic shift of all absorption bands and makes α and β bands equal as a consequence of the expansion of the existing conjugated system of double bonds.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4004629