I2-Mediated Photochemical Preparation of 2-Substituted 1,3-Dioxolanes and Tetrahydrofurans from Alcohols with Polymer-Supported Hypervalent Iodine Reagent, PSDIB

Tomomasa Teduka; Hideo Togo

doi:10.1055/s-2005-864802

LETTER

I₂-Mediated Photochemical Preparation of 2-Substituted 1,3-Dioxolanes and Tetrahydrofurans from Alcohols with Polymer-Supported Hypervalent Iodine Reagent, PSDIB

Tomomasa Teduka^a, Hideo Togo*^a,b
^a Graduate School of Science and Technology, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
^b Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
e-Mail: togo@faculty.chiba-u.jp;

Abstract

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Abstract

Various 2-substituted 1,3-dioxolanes, 1,3-dioxanes, and tetrahydrofurans were obtained selectively in good to moderate yields from the corresponding alcohols with PSDIB in the presence of iodine under irradiation conditions. Moreover, PSDIB was repeatedly used for the same reactions keeping good yield of the cyclic product.

Key words

poly[4-(diacetoxyiodo)styrene] (PSDIB) - 1,3-dioxolane - 1,3-dioxane - tetrahydrofuran - alkoxyl radical - cyclization - iodine - 1,5-H shift

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References

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PSDIB was prepared based on the previous reports (ref. 4).
Poly[4-(diacetoxyiodo)styrene] (PSDIB): IR (KBr): 1630 (br), 1560 (br), 1480, 1410, 1270, 1180, 1000, 760 (br) cm^-1. Found: C, 36.33; H, 3.66; I, 39.19. Loading rate of diacetoxyiodo group is 1.55 mmol/g.

All compounds gave satisfactory spectroscopic data.

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