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Generation and Fate of 1‐Dewar‐pyridin‐3‐olates and ‐2‐olates. Synthesis of 1‐Dewar‐pyridin‐3‐ones
Author(s) -
Maas Gerhard,
Rahm Rainer,
Krebs Fred,
Regitz Manfred,
Stang Peter J.,
Crittell Charles M.
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240729
Subject(s) - chemistry , methyllithium , dimer , yield (engineering) , pyridine , cleavage (geology) , medicinal chemistry , tricyclic , ether , enol , bicyclic molecule , stereochemistry , hexa , organic chemistry , catalysis , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
3‐Oxy‐1‐azabicyclo[2.2.0]hexa‐2,5‐dienes (“3‐oxy‐1‐Dewar‐pyridines”) 6a – d , on cleavage of the enol ether or enol ester function, yield either 1‐azabicyclo[2.2.0]hex‐2‐en‐5‐ones (“1‐Dewar‐pyridin‐3‐ones”) 9 or 2‐azabicyclo[3.1.0]hex‐2‐en‐4‐ones 11 , depending on the substituents and reaction conditions. Ester cleavage of 2‐(benzoyloxy)‐1‐Dewar‐pyridine 7a with methyllithium does not furnish a 1‐Dewar‐2‐pyridinone, but a dimer thereof, namely the tricyclic compound 14 .