title: Synthesis of dibenzocyclohepten-5-ones by electrophilic iodocyclization of 1-([1,1'-biphenyl]-2-yl)alkynones.
abstract: A synthesis of iodo-substituted dibenzocyclohepten-5-ones by the iodine monochloride (or iodine)-induced intramolecular 7-endo-dig cyclization of 1-([1,1'-biphenyl]-2-yl)alkynones is reported. Detailed investigations on the substituent effects during the electrophilic iodocyclization of the alkynones show that they play a crucial role in determining the reaction pathways of the cyclization. By modifying the substitution pattern on the alkynone substrates, the cyclization takes place regioselectively, leading to either dibenzocyclohepten-5-ones, via a 7-endo-dig cyclization, or spiroconjugated compounds, via a 6-endo-dig cyclization.
authors.affiliation: Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York , 65-30 Kissena Boulevard, Flushing, New York 11367, United States.
authors.forename: Yu
authors.initials: Y
authors.lastname: Chen
authors.forename: Chenlong
authors.initials: C
authors.lastname: Huang
authors.forename: Xiaochen
authors.initials: X
authors.lastname: Liu
authors.forename: Eliyahu
authors.initials: E
authors.lastname: Perl
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Chen
authors.forename: Jieun
authors.initials: J
authors.lastname: Namgung
authors.forename: Gopal
authors.initials: G
authors.lastname: Subramaniam
authors.forename: Gan
authors.initials: G
authors.lastname: Zhang
authors.forename: William H
authors.initials: WH
authors.lastname: Hersh
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D003508:Cycloheptanes; D007455:Iodine; C000363:cycloheptanone