Effects of complexation with 18-crown-6 on the hypernucleofugality of phenyl-lambda3-iodanyl groups. Synthesis of vinyl-lambda3-iodane.18-crown-6 complex

Masahito Ochiai; Takashi Suefuji; Kazunori Miyamoto; Motoo Shiro

doi:10.1021/ol050858z

Effects of complexation with 18-crown-6 on the hypernucleofugality of phenyl-lambda3-iodanyl groups. Synthesis of vinyl-lambda3-iodane.18-crown-6 complex

Org Lett. 2005 Jul 7;7(14):2893-6. doi: 10.1021/ol050858z.

Authors

Masahito Ochiai¹, Takashi Suefuji, Kazunori Miyamoto, Motoo Shiro

Affiliation

¹ Faculty of Pharmaceutical Sciences, University of Tokushima, Japan. mochiai@ph2.tokushima-u.ac.jp

PMID: 15987163
DOI: 10.1021/ol050858z

Abstract

[structure: see text] 4-tert-Butyl-1-cyclohexenyl(phenyl)(tetrafluoroborato)-lambda(3)-iodane forms a discrete supramolecular complex by the reaction with 18-crown-6. Solvolysis of the cyclohexenyl-lambda(3)-iodane in the presence of 18-crown-6 indicates that the complexation with 18-crown-6 tends to decrease the leaving group ability of hypervalent phenyl-lambda(3)-iodanyl groups.