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DOI: 10.1055/s-2005-864802
I2-Mediated Photochemical Preparation of 2-Substituted 1,3-Dioxolanes and Tetrahydrofurans from Alcohols with Polymer-Supported Hypervalent Iodine Reagent, PSDIB
Publikationsverlauf
Publikationsdatum:
23. März 2005 (online)
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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
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.