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Synthesis 1988; 1988(11): 862-868
DOI: 10.1055/s-1988-27731
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Halocyclization of Unsaturated Alcohols and Carboxylic Acids Using Bis(sym-collidine)iodine(I) Perchlorate

Robert D. Evans* , Joseph W. Magee, J. Herman Schauble
  • *Department of Chemistry, Villanova University, Villanova, PA 19085, USA
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Publication Date:
20 August 2002 (online)

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Reaction of I(collidine)+ 2 ClO- 4 with unsaturated alcohols and carboxylic acids in dichloromethane at ambient temperature has afforded three- to seven-membered-ring iodoethers and four- to seven-membered-ring iodolactones, respectively, in moderate yields and generally with high regioselectivity. The reaction is of particular utility for synthesis of 2-(1-iodoalkyl)oxiranes and -oxetanes.