ICl-Induced Intramolecular Electrophilic Cyclization of 1-[4′-Methoxy(1,1′-biphenyl)2-yl]alkynones—A Facile Approach to Spiroconjugated Molecules

Authors

  • Prof. Dr. Yu Chen,

    Corresponding author
    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), Fax: (+1) 718-997-5531
    • 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), Fax: (+1) 718-997-5531
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  • Xiaochen Liu,

    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), Fax: (+1) 718-997-5531
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  • Minwook Lee,

    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), Fax: (+1) 718-997-5531
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  • Chenlong Huang,

    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), Fax: (+1) 718-997-5531
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  • Igor Inoyatov,

    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), Fax: (+1) 718-997-5531
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  • Zhiwei Chen,

    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), Fax: (+1) 718-997-5531
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  • Abraham C. Perl,

    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), Fax: (+1) 718-997-5531
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  • Prof. Dr. William H. Hersh

    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), Fax: (+1) 718-997-5531
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Abstract

original image

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.

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