Ontology highlight
ABSTRACT:
SUBMITTER: Ma Y
PROVIDER: S-EPMC7050188 | biostudies-literature | 2019 Jul
REPOSITORIES: biostudies-literature
The Journal of organic chemistry 20190701 14
Aryl carbamates are orthometalated by sodium diisopropylamide (NaDA) in tetrahydrofuran. The resulting arylsodiums undergo Snieckus-Fries rearrangement to give orthoacylated phenols in good yield. The intermediate arylsodiums and resulting orthoacylated phenolates are suggested to be monomeric. The rate-limiting step in the two-step sequence depends on the steric demands of the carbamoyl moiety and the substituents in the meta position of the arene. Rate studies reveal a dominant disolvated-mono ...[more]