ICl-induced intramolecular electrophilic cyclization of 1-[4'-methoxy(1,1'-biphenyl)2-yl]alkynones--a facile approach to spiroconjugated molecules

Yu Chen; Xiaochen Liu; Minwook Lee; Chenlong Huang; Igor Inoyatov; Zhiwei Chen; Abraham C Perl; William H Hersh

doi:10.1002/chem.201301582

ICl-induced intramolecular electrophilic cyclization of 1-[4'-methoxy(1,1'-biphenyl)2-yl]alkynones--a facile approach to spiroconjugated molecules

Chemistry. 2013 Jul 22;19(30):9795-9. doi: 10.1002/chem.201301582. Epub 2013 Jun 13.

Authors

Yu Chen¹, Xiaochen Liu, Minwook Lee, Chenlong Huang, Igor Inoyatov, Zhiwei Chen, Abraham C Perl, William H Hersh

Affiliation

¹ Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, 65-30 Kissena Blvd. Flushing, New York 11367, USA. yu.chen1@qc.cuny.edu

PMID: 23765591
DOI: 10.1002/chem.201301582

Abstract

Spiro compounds: An iodine monochloride-induced intramolecular cyclization of 1-[4'-methoxy(1,1'-biphenyl)2-yl]alkynones has been developed (see scheme). An electrophilic iodocyclization selectively takes place at the ipso position (versus the ortho electrophilic aromatic substitution) to afford 4'H-spiro(cyclohexa[2,5]diene-1,1'-naphthalene)-4,4'-diones, a new group of spiroconjugated compounds.

Keywords: cyclization; electrophilic addition/substitution; iodine monochloride; spiro compounds; substituent effects.