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Cobryketone Derived from Vitamin B12via Palladium-Catalyzed Cleavage of the sp3–sp3 Carbon–Carbon Bond

Author:
Kurcoń, Sylwester, Proinsias, Keith ó, Gryko, Dorota
Source:
Journal of organic chemistry 2013 v.78 no.8 pp. 4115-4122
ISSN:
1520-6904
Subject:
absorption, carbon, catalytic activity, chemical bonding, organic chemistry, palladium, vitamin B12
Abstract:
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.
Agid:
5501252