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Tautomer‐Dependent Bergman Cyclization of Novel Uracil‐Enediyne Chimeras
Author(s) -
Kim ChangSik,
Diez Christian,
Russell Keith C.
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000502)6:9<1555::aid-chem1555>3.0.co;2-m
Subject(s) - enediyne , tautomer , uracil , chemistry , stereochemistry , dna , biochemistry
Uracil‐enediyne chimeras 4, 7 , and 8 were prepared and examined for their propensity to undergo Bergman cyclization. Kinetic experiments showed lactam tautomers 7 and 8 reacted up to 25 times faster than lactim ether 4 . Determination of the activation energy for each cycloaromatization reaction, along with radical trapping agent dependent studies, indicate the rate differences result from different ground state energies of the starting enediynes.