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On mechanistic aspects of 5‐deazaflavin dependent dehydrogenation of alcohol
Author(s) -
Tanaka Kiyoshi,
Kimura Teiji,
Yoneda Fumio,
Ijuin Mineko,
Sakuma Yoshiharu
Publication year - 1987
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.5570240148
Subject(s) - dehydrogenation , chemistry , hydride , deuterium , alcohol , alkoxy group , sodium , medicinal chemistry , potassium , organic chemistry , inorganic chemistry , hydrogen , catalysis , alkyl , physics , quantum mechanics
The reaction of 5‐deazaflavins with alcoholates was investigated and the direct hydride equivalent transfer from C 1 of alcoholates to C 5 of 5‐deazaflavins was confirmed by chemical methods. 5‐Alkoxy‐10‐butyl‐3‐methyl‐5‐deazaflavins were synthesized by treatment of 10‐butyl‐5‐chloro‐3‐methyl‐5‐deazaflavin with the corresponding alcoholates. The 5‐alkoxy‐5‐deazaflavins were reduced by sodium borodeuteride or sodium hydro‐sulfite in deuterium oxide or monodeuteriomethanol to give 10‐butyl‐3‐methyl‐1,5‐dihydro‐5‐deazaflavin‐5,5‐D 2 exclusively. 3,10‐Dimethyl‐5‐deazaflavin radical anion was detected by esr technique on treatment of 3,10‐dimethyl‐5‐deazaflavin with potassium in DMF. From the above reactions, a mechanism of 5‐deazaflavin dependent dehydrogenation of alcoholate was proposed.