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Synthesis 2011(20): 3287-3296  
DOI: 10.1055/s-0030-1260196
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Substitution Alters the Mode of Molecular Iodine-Mediated Intramolecular Cyclization: Syntheses of Benzoxepine and Benzo-2H-pyran Derivatives

Krishna C. Majumdar*a, Inul Ansarya, Biswajit Sinhaa, Brindaban Roya, Balasubramanian Sridharb
a Department of Chemistry, University of Kalyani, Kalyani 741235, West Bengal, India
Fax: +91(33)25828282; e-Mail: kcm_ku@yahoo.co.in;
b Laboratory of X-ray Crystallography, IICT, Hyderabad 500007, India
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Publication History

Received 25 June 2011
Publication Date:
01 September 2011 (online)

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Abstract

The synthesis of benzoxepine and benzo-2H-pyran derivatives by the implementation of an inxepensive and easy to handle molecular iodine-mediated intramolecular electrophilic cyclization strategy is described. Simple substitution at the terminus of the propargyl group alters the course of the iodocyclization.

Key words

iodine - intramolecular cyclization - benzoxepine - benzo­-2H-pyrans

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1

Present address: Department of Chemical Science, Tezpur University, Napaam 784028, Assam, India.

23

CCDC 809665 contains the supplementary crystallographic data for 10a.